Advertisement

Journal of Chemical Crystallography

, Volume 44, Issue 1, pp 30–35 | Cite as

Synthesis and Crystal Structures of (RS,RS,RS)- and (1RS,2RS,3SR)-3-(N-Methylamino)cyclohexane-1,2-diol

  • Stephen G. Davies
  • David S. Hewings
  • Wataru Kurosawa
  • James A. Lee
  • Paul M. Roberts
  • Amber L. Thompson
  • James E. Thomson
Original Paper

Abstract

3-(N-Methylamino)cyclohexane-1,2-diols (RS,RS,RS)-25 and (1RS,2RS,3SR)-26 were synthesised and their crystal structures were studied by X-ray diffraction. Compound 25 co-crystallizes with chloroform in the orthorhombic space group Pna2 1 with cell parameters of a = 11.8550(2) Å, b = 19.8293(4) Å, c = 10.6163(2) Å, V = 2495.64(8) Å3 and Z = 8. Compound 26 crystallizes in the triclinic space group P–1 with cell parameters of a = 13.1019(3) Å, b = 15.0122(3) Å, c = 18.5562(5) Å, α = 95.3082(8)°, β = 90.3738(10)°, γ = 115.2775(9)°, V = 3281.87(14) Å3 and Z = 16. Both structures were characterised by arrays of hydrogen bonding interactions.

Graphical Abstract

(RS,RS,RS)-3-(N-Methylamino)cyclohexane-1,2-diol and (1RS,2RS,3SR)-3-(N-Methylamino)cyclohexane-1,2-diol were synthesised and their structures were studied by X-ray diffraction.

Keywords

Amino diol Hydrogen bonding Chemoselective Diastereoselective Dihydroxylation 

Notes

Acknowledgments

The authors would like to thank Ajinomoto Co., Inc. for funding (W.K.).

References

  1. 1.
    Davies SG, Ling KB, Roberts PM, Russell AJ, Thomson JE, Woods PA (2010) Tetrahedron 66:6806CrossRefGoogle Scholar
  2. 2.
    Davies SG, Ling KB, Roberts PM, Russell AJ, Thomson JE (2007) Chem Commun 39:4029CrossRefGoogle Scholar
  3. 3.
    Csatayová K, Davies SG, Lee JA, Ling KB, Roberts PM, Russell AJ, Thomson JE (2010) Org Lett 12:3152CrossRefGoogle Scholar
  4. 4.
    Csatayová K, Davies SG, Lee JA, Ling KB, Roberts PM, Russell AJ, Thomson JE (2010) Tetrahedron 66:8420CrossRefGoogle Scholar
  5. 5.
    Christensen KE, Csatayová K, Davies SG, Lee JA, Roberts PM, Thompson AL, Thomson JE (2011) J Chem Crystallogr 41:1007CrossRefGoogle Scholar
  6. 6.
    Aciro C, Claridge TDW, Davies SG, Roberts PM, Russell AJ, Thomson JE (2008) Org Biomol Chem 6:3751CrossRefGoogle Scholar
  7. 7.
    Aciro C, Davies SG, Roberts PM, Russell AJ, Smith AD, Thomson JE (2008) Org Biomol Chem 6:3762CrossRefGoogle Scholar
  8. 8.
    Aciro C, Davies SG, Kurosawa W, Roberts PM, Russell AJ, Thomson JE (2009) Org Lett 11:1333CrossRefGoogle Scholar
  9. 9.
    Bond CW, Cresswell AJ, Davies SG, Fletcher AM, Kurosawa W, Lee JA, Roberts PM, Russell AJ, Smith AD, Thomson JE (2009) J Org Chem 74:6735CrossRefGoogle Scholar
  10. 10.
    Bagal SK, Davies SG, Lee JA, Roberts PM, Russell AJ, Scott PM, Thomson JE (2010) Org Lett 12:136CrossRefGoogle Scholar
  11. 11.
    Davies SG, Fletcher AM, Kurosawa W, Lee JA, Poce G, Roberts PM, Thomson JE, Williamson DM (2010) J Org Chem 75:7745CrossRefGoogle Scholar
  12. 12.
    Bagal SK, Davies SG, Lee JA, Roberts PM, Scott PM, Thomson JE (2010) J Org Chem 75:8133CrossRefGoogle Scholar
  13. 13.
    Kurosawa W, Roberts PM, Davies SG (2010) Yuki Gosei Kagaku Kyokaishi (J Synth Org Chem Jpn) 68:1295CrossRefGoogle Scholar
  14. 14.
    Bagal SK, Davies SG, Fletcher AM, Lee JA, Roberts PM, Scott PM, Thomson JE (2011) Tetrahedron Lett 52:2216CrossRefGoogle Scholar
  15. 15.
    Cresswell AJ, Davies SG, Lee JA, Morris MJ, Roberts PM, Thomson JE (2012) J Org Chem 77:7262CrossRefGoogle Scholar
  16. 16.
    Brennan MB, Claridge TDW, Compton RG, Davies SG, Fletcher AM, Henstridge MC, Hewings DS, Kurosawa W, Lee JA, Roberts PM, Schoonen AK, Thomson JE (2012) J Org Chem 77:7241CrossRefGoogle Scholar
  17. 17.
    Cosier J, Glazer AM (1986) J Appl Crystallogr 19:105CrossRefGoogle Scholar
  18. 18.
    Otwinowski Z, Minor W (1997) Methods in enzymology. Academic Press, New York, pp 307–326Google Scholar
  19. 19.
    Altomare A, Cascarano G, Giacovazzo C, Guagliardi A, Burla MC, Polidori G, Camalli M (1994) J Appl Crystallogr 27:435Google Scholar
  20. 20.
    Betteridge PW, Carruthers JR, Cooper RI, Prout CK, Watkin DJ (2003) J Appl Crystallogr 36:1487CrossRefGoogle Scholar
  21. 21.
    Cooper RI, Thompson AL, Watkin DJ (2010) J Appl Cryst 43:1100CrossRefGoogle Scholar
  22. 22.
    Thompson AL, Watkin DJ (2011) J Appl Crystallogr 44:1017CrossRefGoogle Scholar
  23. 23.
    Flack HD (1983) Acta Crystallogr A 39:876CrossRefGoogle Scholar
  24. 24.
    Thompson AL, Watkin DJ (2009) Tetrahedron Asymmetry 20:712–717CrossRefGoogle Scholar
  25. 25.
    Flack HD, Bernardinelli G (2000) J Appl Crystallogr 33:1143CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Stephen G. Davies
    • 1
  • David S. Hewings
    • 1
  • Wataru Kurosawa
    • 1
  • James A. Lee
    • 1
  • Paul M. Roberts
    • 1
  • Amber L. Thompson
    • 1
  • James E. Thomson
    • 1
  1. 1.Chemistry Research Laboratory, Department of ChemistryUniversity of OxfordOxfordUK

Personalised recommendations