(9S,13R,14R)-7,8-Didehydro-3,4,7-trimeth­oxy-17-methyl­morphinan-6-one

Li, Y.-F.; Qian, Y.; Yin, L.-H.; Lv, R.; Zhu, H.-J.

doi:10.1107/S1600536808040749

Volume 65
Part 4
Page o689
April 2009

Received 23 October 2008
Accepted 3 December 2008
Online 6 March 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R = 0.070
wR = 0.208
Data-to-parameter ratio = 7.6
Details

(9S,13R,14R)-7,8-Didehydro-3,4,7-trimethoxy-17-methylmorphinan-6-one

Yu-Feng Li,^a Yi Qian,^a Li-He Yin,^a Ran Lv ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: zhuhj@njut.edu.cn

The title compound, C₂₀H₂₅NO₄, was synthesized by a Mitsunobu reaction of sinomenine [(9S,13R,14R)-7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one] with methanol. The chiral centers were unchanged during the reaction. Intramolecular C-HO hydrogen bonds result in the formation of six-membered rings.

Related literature

For the anti-inflammatory, antitussive and antiarrgythmic activities of sinomenine, see: Wang & Li (1965).

Experimental

Crystal data

C₂₀H₂₅NO₄
M_r = 343.41
Trigonal, P 3₂
a = 10.9590 (15) Å
c = 12.726 (3) Å
V = 1323.6 (4) Å³
Z = 3
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.40 × 0.30 × 0.30 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.965, T_max = 0.974
2008 measured reflections
1728 independent reflections
1281 reflections with I > 2(I)
R_int = 0.037
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2(F²)] = 0.070
wR(F²) = 0.208
S = 1.06
1728 reflections
226 parameters
44 restraints
H-atom parameters constrained
_max = 0.45 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5AO1	0.97	2.23	2.853 (9)	121
C16-H16BO1	0.97	2.53	3.102 (10)	118
C18-H18BO2	0.96	2.14	2.812 (16)	126

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2561 ).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft. The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, N. Q. & Li, Y. S. (1965). Acta Pharm. Sin. 12, 86-87.

organic compounds