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Volume 69 
Part 6 
Page o935  
June 2013  

Received 8 May 2013
Accepted 16 May 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.101
Data-to-parameter ratio = 10.8
Details
Open access

tert-Butyl N-[(3R,4R)-1-(2-cyanoacetyl)-4-methylpiperidin-3-yl]-N-methylcarbamate

aEberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and bUniversity Mainz, Institut of Organic Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: stefan.laufer@uni-tuebingen.de

The piperidine ring of the title compound, C15H25N3O3, adopts a slightly distorted chair conformation with the cis substituents displaying an N-C-C-C torsion angle of 43.0 (3)°. The cyano group (plane defined by C-C-C[triple bond]N atoms) is bent slightly out of the plane of the amide group by 13.3 (2)°. The carbamate group is oriented at a dihedral angle of 60.3 (5)° relative to the amide group.

Related literature

For the biological activity and structure-activity relationships of Tofacitinib {systematic name: 3-[(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile} derivatives, see: Changelian et al. (2003[Changelian, P. S., et al. (2003). Science, 302, 875-878.]); Flanagan et al. (2010[Flanagan, M. E., et al. (2010). J. Med. Chem. 53, 8468-8484.]); Zerbini & Lomonte (2012[Zerbini, C. A. & Lomonte, A. B. (2012). Expert Rev. Clin. Immunol. 8, 319-331.]). For details of the synthesis, see: Babu et al. (2010[Babu, Y. S., Chand, P., Kotian, P. L. & Kumar, V. S. (2010). World Patent 2010014930.]).

[Scheme 1]

Experimental

Crystal data
  • C15H25N3O3

  • Mr = 295.38

  • Monoclinic, P 21

  • a = 7.1786 (11) Å

  • b = 7.3213 (10) Å

  • c = 16.042 (2) Å

  • [beta] = 102.196 (4)°

  • V = 824.1 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.60 × 0.35 × 0.10 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • 5061 measured reflections

  • 2115 independent reflections

  • 1818 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.101

  • S = 1.03

  • 2115 reflections

  • 195 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2311 ).


Acknowledgements

The authors thank Ellen Pfaffenrot and Peter Keck for fruitful discussions and suggestions and acknowledge support by the Deutsche Forschungsgemeinschaft and the Open Access Publishing Fund of Tübingen University.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Babu, Y. S., Chand, P., Kotian, P. L. & Kumar, V. S. (2010). World Patent 2010014930.
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Changelian, P. S., et al. (2003). Science, 302, 875-878.  [ISI] [CrossRef] [PubMed] [ChemPort]
Flanagan, M. E., et al. (2010). J. Med. Chem. 53, 8468-8484.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Zerbini, C. A. & Lomonte, A. B. (2012). Expert Rev. Clin. Immunol. 8, 319-331.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o935  [ doi:10.1107/S1600536813013512 ]

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