Bruceolline J: 2-hy­droxy-3,3-dimethyl-2,3-di­hydro­cyclo­penta­[b]indol-1(4H)-one

Lopchuk, J.M.; Gribble, G.W.; Millikan, S.P.; Jasinski, J.P.

doi:10.1107/S1600536813020527

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1351-o1352

doi:10.1107/S1600536813020527

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Bruceolline J: 2-hydroxy-3,3-dimethyl-2,3-dihydrocyclopenta[b]indol-1(4H)-one

Justin M. Lopchuk,^a Gordon W. Gribble,^a Sean P. Millikan ^b and Jerry P. Jasinski ^b ^*

^aDepartment of Chemistry, Dartmouth College, Hanover, NH 03755-3564, USA, and ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

(Received 20 July 2013; accepted 23 July 2013; online 31 July 2013)

The 12-membered cyclopenta[b]indole ring system in the title compound, C₁₃H₁₃NO₂, deviates only slightly from planarity (r.m.s. deviation = 0.051 Å). In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the molecules into sheets parallel to (100). The five-membered cyclopentanone ring is in slightly distorted envelope conformation with the C atom bearing the hydroxy substituent as the flap.

Related literature

For a review of compounds isolated from Brucea sp. plants, see: Liu et al. (2009 ). For the first isolation of bruceolline J, see: Chen et al. (2011 ). For the DDQ-mediated selective oxidation of indole side chains, see: Oikawa & Yonemitsu (1977 ). For examples of the reduction of α-keto esters with sodium borohydride, see Dalla et al. (1999 ). For the enantioselective reduction of related sterically hindered ketones with β-chlorodiisopinocampheylborane, see: Brown et al. (1986 ). For the isolation of related bruceollines, see: Ouyang et al. (1994a ,b , 1995 ). For the crystal structure of bruceolline D, see: Lopchuk et al. (2013 ). For the total synthesis and crystal structure of bruceolline E, see: Jordan et al. (2011 , 2012). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₁₃NO₂
M_r = 215.24
Monoclinic, P 2₁ /c
a = 8.2951 (3) Å
b = 12.3070 (4) Å
c = 10.7340 (4) Å
β = 97.207 (3)°
V = 1087.15 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.44 × 0.38 × 0.34 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.782, T_max = 1.000
13545 measured reflections
3753 independent reflections
2888 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.134
S = 1.04
3753 reflections
148 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.84	1.90	2.7245 (12)	168
N1—H1⋯O2ⁱⁱ	0.88	1.91	2.7500 (12)	158
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813020527/bt6922sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813020527/bt6922Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813020527/bt6922Isup3.cml

checkCIF report

Comment top

Bruceolline J is a cyclopenta[b]indole alkaloid which has been recently isolated from the stems of Brucea mollis Wall (Chen et al., 2011). Our total synthesis of racemic bruceolline J was achieved by the oxidation of bruceolline D to bruceolline E with DDQ followed by the selective reduction of bruceolline E with sodium borohydride in 98% yield. Enantioselective reductions with β-chlorodiisopinocampheylborane gave both the natural and unnatural enantiomers in excellent yields and enantioselectivites. Further isolation studies of the Brucea mollis shrubs have resulted in the discovery of a myriad of other bruceollines and cathan-6-one alkaloids (Ouyang et al., 1994a; Ouyang et al., 1994b; Ouyang et al., 1995). Although there has been limited attention from the synthetic community given to these compounds, a previous synthesis of bruceolline E has been reported (Jordan et al., 2011). The crystal structures of bruceolline D (Lopchuk et al., 2013) and bruceolline E (Jordon et al., 2012) have been disclosed. In view of the importance of cyclopenta[b]indole alkaloids, we report here the crystal structure of the title compound, C₁₃H₁₃NO₂, (I).

The title compound, crystallizes with one molecule in the asymmetric unit. The 12-membered cyclopenta[b]indole ring system deviates only slightly from planarity (r.m.s. deviation 0.051Å) (Fig. 1). The 5-membered cyclopentanone ring is in slightly distorted envelope configuration (Q= 0.1012 (12)Å, ϕ = 66.4 (7)°) with C3 as the flap Bond lengths are in normal ranges (Allen et al., 1987). In the crystal N—H···O and O—H···O hydrogen bonds (Table 1) link the molecules into sheets parallel to (1 0 0) and contribute to crystal packing stability (Fig. 2).

Related literature top

For a review of compounds isolated from Brucea sp. plants, see: Liu et al. (2009). For the first isolation of bruceolline J, see: Chen et al. (2011). For the DDQ-mediated selective oxidation of indole side chains, see: Oikawa & Yonemitsu (1977). For examples of the reduction of α-keto esters with sodium borohydride, see Dalla et al. (1999). For the enantioselective reduction of related sterically hindered ketones with β-chlorodiisopinocampheylborane, see: Brown et al. (1986). For the isolation of related bruceollines, see: Ouyang et al. (1994a,b, 1995). For the crystal structure of bruceolline D, see: Lopchuk et al. (2013). For the total synthesis and crystal structure of bruceolline E, see: Jordan et al. (2011, 2012). For bond-length data, see: Allen et al. (1987).

Experimental top

To an ice-cold solution of bruceolline E (50 mg, 0.234 mmol, 1.0 equiv.) in dry THF (10 mL) was added sodium borohydride (5 mg, 0.117 mmol, 0.5 equiv.) in one portion (Fig. 3). After stirring at 0°C for 5 minutes, the reaction was quenched with water (5 mL) and concentrated to half the original volume. The mixture was extracted with ethyl acetate (3 x 40 mL). The organic extracts were combined, dried over Na₂SO₄, and concentrated in vacuo to an off-white solid. The residue was purified by flash chromatography (50% ethyl acetate in pentane) to afford the desired product (I) as a white solid (50 mg, 98% yield). Single crystals suitable for diffraction were grown from ethyl acetate (slow evaporation) at ambient temperature [m.p. 466-467 K (dec); no literature value available].

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the b axis. Dashed lines indicate N—H···O and O—H···O hydrogen bonds forming sheets parallel to (1 0 0). H atoms not involved hydrogen bonding have been deleted for clarity.
	Fig. 3. Synthesis of (I).

2-Hydroxy-3,3-dimethyl-2,3-dihydrocyclopenta[b]indol-1(4H)-one top

Crystal data top

C₁₃H₁₃NO₂	F(000) = 456
M_r = 215.24	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
a = 8.2951 (3) Å	Cell parameters from 3528 reflections
b = 12.3070 (4) Å	θ = 3.3–32.9°
c = 10.7340 (4) Å	µ = 0.09 mm⁻¹
β = 97.207 (3)°	T = 173 K
V = 1087.15 (7) Å³	Irregular, colourless
Z = 4	0.44 × 0.38 × 0.34 mm

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	3753 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2888 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 16.0416 pixels mm^-1	θ_max = 33.0°, θ_min = 3.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −17→18
T_min = 0.782, T_max = 1.000	l = −16→15
13545 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.134	w = 1/[σ²(F_o²) + (0.0662P)² + 0.2062P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3753 reflections	Δρ_max = 0.40 e Å⁻³
148 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Crystal data top

C₁₃H₁₃NO₂	V = 1087.15 (7) Å³
M_r = 215.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2951 (3) Å	µ = 0.09 mm⁻¹
b = 12.3070 (4) Å	T = 173 K
c = 10.7340 (4) Å	0.44 × 0.38 × 0.34 mm
β = 97.207 (3)°

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	3753 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	2888 reflections with I > 2σ(I)
T_min = 0.782, T_max = 1.000	R_int = 0.035
13545 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.04	Δρ_max = 0.40 e Å⁻³
3753 reflections	Δρ_min = −0.25 e Å⁻³
148 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.83909 (11)	0.55666 (6)	0.93513 (8)	0.03008 (19)
O2	1.13253 (11)	0.51818 (7)	0.82424 (8)	0.0297 (2)
H2	1.1552	0.4933	0.8972	0.045*
N1	0.76891 (11)	0.21451 (7)	0.76238 (9)	0.0246 (2)
H1	0.7945	0.1602	0.7152	0.030*
C1	0.83979 (13)	0.31258 (8)	0.77083 (10)	0.0221 (2)
C2	0.98429 (13)	0.35821 (9)	0.71904 (10)	0.0233 (2)
C3	0.98044 (14)	0.47719 (8)	0.77069 (10)	0.0242 (2)
H3	0.9398	0.5254	0.6986	0.029*
C4	0.85291 (13)	0.47926 (8)	0.86414 (9)	0.0230 (2)
C5	0.76844 (13)	0.37877 (9)	0.85201 (10)	0.0233 (2)
C6	0.64335 (13)	0.31588 (9)	0.90039 (10)	0.0239 (2)
C7	0.53565 (14)	0.33227 (11)	0.98851 (11)	0.0301 (2)
H7	0.5298	0.4006	1.0290	0.036*
C8	0.43771 (15)	0.24690 (12)	1.01561 (13)	0.0365 (3)
H8	0.3650	0.2567	1.0764	0.044*
C9	0.44313 (15)	0.14681 (12)	0.95594 (14)	0.0383 (3)
H9	0.3739	0.0899	0.9768	0.046*
C10	0.54722 (15)	0.12837 (10)	0.86689 (13)	0.0333 (3)
H10	0.5498	0.0604	0.8252	0.040*
C11	0.64742 (13)	0.21344 (9)	0.84131 (10)	0.0249 (2)
C12	1.13707 (14)	0.29740 (10)	0.77445 (12)	0.0309 (2)
H12A	1.2332	0.3343	0.7503	0.046*
H12B	1.1332	0.2228	0.7424	0.046*
H12C	1.1429	0.2961	0.8662	0.046*
C13	0.96704 (18)	0.35481 (12)	0.57537 (11)	0.0364 (3)
H13A	0.8664	0.3917	0.5411	0.055*
H13B	0.9636	0.2790	0.5471	0.055*
H13C	1.0601	0.3916	0.5460	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0424 (5)	0.0199 (4)	0.0285 (4)	0.0036 (3)	0.0066 (3)	−0.0047 (3)
O2	0.0386 (5)	0.0241 (4)	0.0273 (4)	−0.0099 (3)	0.0075 (3)	0.0006 (3)
N1	0.0267 (4)	0.0190 (4)	0.0284 (4)	0.0002 (3)	0.0046 (3)	−0.0042 (3)
C1	0.0248 (5)	0.0199 (4)	0.0216 (4)	0.0009 (4)	0.0033 (3)	−0.0015 (4)
C2	0.0279 (5)	0.0229 (5)	0.0197 (4)	−0.0015 (4)	0.0056 (4)	−0.0019 (4)
C3	0.0332 (6)	0.0189 (4)	0.0210 (5)	−0.0019 (4)	0.0051 (4)	0.0009 (4)
C4	0.0303 (5)	0.0184 (4)	0.0201 (4)	0.0036 (4)	0.0023 (4)	0.0001 (3)
C5	0.0266 (5)	0.0210 (5)	0.0228 (5)	0.0021 (4)	0.0056 (4)	−0.0008 (4)
C6	0.0233 (5)	0.0238 (5)	0.0245 (5)	0.0022 (4)	0.0027 (4)	0.0020 (4)
C7	0.0265 (5)	0.0358 (6)	0.0289 (5)	0.0046 (4)	0.0064 (4)	0.0019 (5)
C8	0.0271 (6)	0.0474 (7)	0.0364 (6)	0.0022 (5)	0.0090 (5)	0.0099 (6)
C9	0.0282 (6)	0.0386 (7)	0.0485 (8)	−0.0043 (5)	0.0068 (5)	0.0136 (6)
C10	0.0293 (6)	0.0262 (6)	0.0436 (7)	−0.0029 (4)	0.0022 (5)	0.0052 (5)
C11	0.0232 (5)	0.0227 (5)	0.0283 (5)	0.0013 (4)	0.0017 (4)	0.0023 (4)
C12	0.0276 (6)	0.0250 (5)	0.0405 (6)	0.0014 (4)	0.0062 (4)	−0.0033 (5)
C13	0.0477 (7)	0.0408 (7)	0.0217 (5)	−0.0070 (6)	0.0080 (5)	−0.0050 (5)

Geometric parameters (Å, º) top

O1—C4	1.2341 (13)	C6—C11	1.4136 (15)
O2—H2	0.8400	C7—H7	0.9500
O2—C3	1.4122 (14)	C7—C8	1.3812 (19)
N1—H1	0.8800	C8—H8	0.9500
N1—C1	1.3406 (13)	C8—C9	1.392 (2)
N1—C11	1.3956 (14)	C9—H9	0.9500
C1—C2	1.4928 (15)	C9—C10	1.3849 (19)
C1—C5	1.3793 (14)	C10—H10	0.9500
C2—C3	1.5675 (15)	C10—C11	1.3854 (16)
C2—C12	1.5267 (16)	C12—H12A	0.9800
C2—C13	1.5313 (15)	C12—H12B	0.9800
C3—H3	1.0000	C12—H12C	0.9800
C3—C4	1.5467 (15)	C13—H13A	0.9800
C4—C5	1.4194 (15)	C13—H13B	0.9800
C5—C6	1.4425 (15)	C13—H13C	0.9800
C6—C7	1.3948 (15)

C3—O2—H2	109.5	C6—C7—H7	120.8
C1—N1—H1	125.9	C8—C7—C6	118.46 (12)
C1—N1—C11	108.15 (9)	C8—C7—H7	120.8
C11—N1—H1	125.9	C7—C8—H8	119.2
N1—C1—C2	132.79 (9)	C7—C8—C9	121.50 (12)
N1—C1—C5	110.80 (10)	C9—C8—H8	119.2
C5—C1—C2	116.19 (9)	C8—C9—H9	119.3
C1—C2—C3	99.60 (8)	C10—C9—C8	121.45 (11)
C1—C2—C12	109.66 (9)	C10—C9—H9	119.3
C1—C2—C13	112.76 (9)	C9—C10—H10	121.5
C12—C2—C3	111.89 (9)	C9—C10—C11	117.03 (12)
C12—C2—C13	110.31 (10)	C11—C10—H10	121.5
C13—C2—C3	112.23 (9)	N1—C11—C6	108.88 (9)
O2—C3—C2	114.89 (9)	C10—C11—N1	128.63 (11)
O2—C3—H3	107.5	C10—C11—C6	122.44 (11)
O2—C3—C4	112.27 (8)	C2—C12—H12A	109.5
C2—C3—H3	107.5	C2—C12—H12B	109.5
C4—C3—C2	106.90 (8)	C2—C12—H12C	109.5
C4—C3—H3	107.5	H12A—C12—H12B	109.5
O1—C4—C3	122.49 (10)	H12A—C12—H12C	109.5
O1—C4—C5	130.25 (10)	H12B—C12—H12C	109.5
C5—C4—C3	107.22 (8)	C2—C13—H13A	109.5
C1—C5—C4	109.06 (9)	C2—C13—H13B	109.5
C1—C5—C6	107.19 (10)	C2—C13—H13C	109.5
C4—C5—C6	143.48 (10)	H13A—C13—H13B	109.5
C7—C6—C5	135.84 (11)	H13A—C13—H13C	109.5
C7—C6—C11	119.12 (10)	H13B—C13—H13C	109.5
C11—C6—C5	104.97 (9)

O1—C4—C5—C1	−172.60 (11)	C4—C5—C6—C11	−173.69 (15)
O1—C4—C5—C6	0.2 (2)	C5—C1—C2—C3	−7.02 (12)
O2—C3—C4—O1	41.66 (14)	C5—C1—C2—C12	110.49 (11)
O2—C3—C4—C5	−136.56 (9)	C5—C1—C2—C13	−126.17 (11)
N1—C1—C2—C3	178.95 (11)	C5—C6—C7—C8	−175.79 (12)
N1—C1—C2—C12	−63.53 (15)	C5—C6—C11—N1	0.33 (12)
N1—C1—C2—C13	59.81 (16)	C5—C6—C11—C10	177.91 (11)
N1—C1—C5—C4	176.56 (9)	C6—C7—C8—C9	−0.91 (19)
N1—C1—C5—C6	1.03 (13)	C7—C6—C11—N1	−177.07 (10)
C1—N1—C11—C6	0.28 (12)	C7—C6—C11—C10	0.51 (17)
C1—N1—C11—C10	−177.10 (12)	C7—C8—C9—C10	0.1 (2)
C1—C2—C3—O2	134.83 (9)	C8—C9—C10—C11	0.97 (19)
C1—C2—C3—C4	9.56 (10)	C9—C10—C11—N1	175.78 (11)
C1—C5—C6—C7	175.93 (13)	C9—C10—C11—C6	−1.28 (18)
C1—C5—C6—C11	−0.81 (12)	C11—N1—C1—C2	173.45 (11)
C2—C1—C5—C4	1.24 (13)	C11—N1—C1—C5	−0.82 (12)
C2—C1—C5—C6	−174.29 (9)	C11—C6—C7—C8	0.61 (17)
C2—C3—C4—O1	168.51 (10)	C12—C2—C3—O2	19.00 (12)
C2—C3—C4—C5	−9.72 (11)	C12—C2—C3—C4	−106.28 (10)
C3—C4—C5—C1	5.44 (12)	C13—C2—C3—O2	−105.63 (11)
C3—C4—C5—C6	178.25 (14)	C13—C2—C3—C4	129.09 (10)
C4—C5—C6—C7	3.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.84	1.90	2.7245 (12)	168
N1—H1···O2ⁱⁱ	0.88	1.91	2.7500 (12)	158

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.84	1.90	2.7245 (12)	168.2
N1—H1···O2ⁱⁱ	0.88	1.91	2.7500 (12)	157.8

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, y−1/2, −z+3/2.

Acknowledgements

JML acknowledges support from a Graduate Assistance in Areas of National Need (GAANN) fellowship. GWG acknowledges support by the Donors of the Petroleum Research Fund (PRF), administered by the American Chemical Society, and by Wyeth. JPJ acknowledges the NSF MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1351-o1352

doi:10.1107/S1600536813020527

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bruceolline J: 2-hy­dr­oxy-3,3-di­methyl-2,3-di­hydro­cyclo­penta­[b]indol-1(4H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Bruceolline J: 2-hydroxy-3,3-dimethyl-2,3-dihydrocyclopenta[b]indol-1(4H)-one