Selective Reduction of a,b-Unsaturated Steroidal Carbonyl Compounds by NaBH4 in Presence of Guanidine Hydrochloride in Dioxane

Salman Ahmad Khan; Abdullah M. Asiri

doi:10.14233/ajchem.2014.16363

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Issue Published : September 16, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Selective Reduction of a,b-Unsaturated Steroidal Carbonyl Compounds by NaBH4 in Presence of Guanidine Hydrochloride in Dioxane

https://doi.org/10.14233/ajchem.2014.16363

Salman Ahmad Khan

Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia

Abdullah M. Asiri

Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia; Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia

Corresponding Author(s) : Salman Ahmad Khan

sahmad_phd@yahoo.co.in

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19
Article Published : September 18, 2014

Abstract

A selective hydrogenation of a,b-unsaturated steroidal carbonyl compounds with NaBH₄ in the presence of guanidine hydrochloride in dioxane in good to excellent yields are described.

Keywords

Guanidine Steroids Dioxane Reduction

Ahmad Khan, S., & M. Asiri, A. (2014). Selective Reduction of a,b-Unsaturated Steroidal Carbonyl Compounds by NaBH4 in Presence of Guanidine Hydrochloride in Dioxane. Asian Journal of Chemistry, 26(19), 6331–6334. https://doi.org/10.14233/ajchem.2014.16363

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References

R.A.W. Johnstone, A.H. Wilby and I.D. Entwistle, Chem. Rev., 85, 129 (1985); doi:10.1021/cr00066a003.
R.M. Kellogg, In Comprehensive Organic Synthesis, Pergamon: Oxford, Vol. 8, Chapter 1.3 (1991).
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J.T. Hynes, J.P. Klinman, H.H. Limbach and R.L.E. Schowen, Hydrogen Transfer Reactions Wiley-VCH: Weinheim, 2007.
T. Ohkuma, R. Noyori, E.N. Jacobsen, A. Pfaltz and H.E. Yamamoto, In Comprehensive Asymmetric Catalysis; Springer: Berlin, vol. I, p. 227 (1999).
S. Gladiali, G. Mestroni, M. Beller and C. Bolm, Transition Metals for Organic Synthesis, Wiley-VCH: Weinheim, 2, Chapter 1.3 (2004).
S. Enthaler, R. Jackstell, B. Hagemann, K. Junge, G. Erre and M. Beller, J. Organomet. Chem., 691, 4652 (2006); doi:10.1016/j.jorganchem.2006.07.013.
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R. Noyori and S. Hashiguchi, Acc. Chem. Res., 30, 97 (1997); doi:10.1021/ar9502341.
T. Ikariya, K. Murata and R. Noyori, Org. Biomol. Chem., 4, 393 (2006); doi:10.1039/b513564h.
S. Gladiali and E. Alberico, Chem. Soc. Rev., 35, 226 (2006); doi:10.1039/b513396c.
R. Noyori, M. Yamakawa and S. Hashiguchi, J. Org. Chem., 66, 7931 (2001); doi:10.1021/jo010721w.
S.E. Clapham, A. Hadzovic and R.H. Morris, Coord. Chem. Rev., 248, 2201 (2004); doi:10.1016/j.ccr.2004.04.007.
J.S.M. Samec, J.E. Backwall, P.G. Andersson and P. Brandt, Chem. Soc. Rev., 35, 237 (2006); doi:10.1039/b515269k.
K. Kaneda, K. Ebitani, T. Mizugaki and K. Mori, Bull. Chem. Soc. Jpn., 79, 981 (2006); doi:10.1246/bcsj.79.981.
M.D. Le Page and B.R. James, Chem. Commun., 1647 (2000); doi:10.1039/b005338o.
P. Phukan and A. Sudalai, Synth. Commun., 30, 2401 (2000); doi:10.1080/00397910008086882.
G.P. Boldrini, D. Savoia, E. Tagliavini, C. Trombini and A. Umani-Ronchi, J. Org. Chem., 50, 3082 (1985); doi:10.1021/jo00217a014.
T.T. Upadhya, S.P. Katdare, D.P. Sabde, V. Ramaswamy and A. Sudalai, Chem. Commun., 1119 (1997); doi:10.1039/a701518f.
S.K. Mohapatra, S.U. Sonavane, R.V. Jayaram and P. Selvam, Org. Lett., 4, 4297 (2002); doi:10.1021/ol026936p.
B.-C. Chen, J.E. Sundeen, P. Guo, M.S. Bednarz and R. Zhao, Tetrahedron Lett., 42, 1245 (2001); doi:10.1016/S0040-4039(00)02257-7.
T. Suwa, E. Sugiyama, I. Shibata and A. Baba, Synthesis, 789 (2000); doi:10.1055/s-2000-6273.
C.F. Lane, Synthesis, 135 (1975); doi:10.1055/s-1975-23685.
A.F. Abdel-Magid, K.G. Carson, B.D. Harris, C.A. Maryanoff and R.D. Shah, J. Org. Chem., 61, 3849 (1996); doi:10.1021/jo960057x.
M.D. Bomann, I.C. Guch and M.A. Dimare, J. Org. Chem., 60, 5995 (1995); doi:10.1021/jo00123a049.
A. Heydari, S. Khaksar, J. Akbari, M. Esfandyari, M. Pourayoubi and Tajbakhsh, Tetrahedron Lett., 48, 1135 (2007); doi:10.1016/j.tetlet.2006.12.069.
P.N. Rylabder, Hydrogenation Methods, Academic Press, New York (1985).
R.F. Borch, M.D. Bernstein and H.D. Durst, J. Am. Chem. Soc., 93, 2897 (1971); doi:10.1021/ja00741a013.
J.L. Luche, L. Rodriguza-Hahn and P. Crabbe, Chem. Commun., 601 (1978); doi:10.1039/c39780000601.
T. Kawakami, M. Miyatake, I. Shibata and A. Baba, J. Org. Chem., 61, 376 (1996); doi:10.1021/jo951500r.
J.C. Fuller, E.L. Stangeland, C.T. Goralski and B. Singaram, Tetrahedron Lett., 34, 257 (1993); doi:10.1016/S0040-4039(00)60561-0.
B.C. Ranu and A.R. Das, J. Org. Chem., 56, 4796 (1991); doi:10.1021/jo00015a042.
S.A. Khan, A.M. Asiri and K. Sharma, Med. Chem. Res., 22, 1998 (2013); doi:10.1007/s00044-012-0155-2.
A.M. Asiri and S.A. Khan, Molecules, 15, 4784 (2010); doi:10.3390/molecules15074784.

References

R.A.W. Johnstone, A.H. Wilby and I.D. Entwistle, Chem. Rev., 85, 129 (1985); doi:10.1021/cr00066a003.

R.M. Kellogg, In Comprehensive Organic Synthesis, Pergamon: Oxford, Vol. 8, Chapter 1.3 (1991).

J.E. Backvall, J. Organomet. Chem., 652, 105 (2002); doi:10.1016/S0022-328X(02)01316-5.

J.T. Hynes, J.P. Klinman, H.H. Limbach and R.L.E. Schowen, Hydrogen Transfer Reactions Wiley-VCH: Weinheim, 2007.

T. Ohkuma, R. Noyori, E.N. Jacobsen, A. Pfaltz and H.E. Yamamoto, In Comprehensive Asymmetric Catalysis; Springer: Berlin, vol. I, p. 227 (1999).

S. Gladiali, G. Mestroni, M. Beller and C. Bolm, Transition Metals for Organic Synthesis, Wiley-VCH: Weinheim, 2, Chapter 1.3 (2004).

S. Enthaler, R. Jackstell, B. Hagemann, K. Junge, G. Erre and M. Beller, J. Organomet. Chem., 691, 4652 (2006); doi:10.1016/j.jorganchem.2006.07.013.

X. Wu, J. Liu, X. Li, A. Zanotti-Gerosa, F. Hancock, D. Vinci, J. Ruan and J. Xiao, Angew. Chem. Int. Ed., 45, 6718 (2006); doi:10.1002/anie.200602122.

R. Noyori and S. Hashiguchi, Acc. Chem. Res., 30, 97 (1997); doi:10.1021/ar9502341.

T. Ikariya, K. Murata and R. Noyori, Org. Biomol. Chem., 4, 393 (2006); doi:10.1039/b513564h.

S. Gladiali and E. Alberico, Chem. Soc. Rev., 35, 226 (2006); doi:10.1039/b513396c.

R. Noyori, M. Yamakawa and S. Hashiguchi, J. Org. Chem., 66, 7931 (2001); doi:10.1021/jo010721w.

S.E. Clapham, A. Hadzovic and R.H. Morris, Coord. Chem. Rev., 248, 2201 (2004); doi:10.1016/j.ccr.2004.04.007.

J.S.M. Samec, J.E. Backwall, P.G. Andersson and P. Brandt, Chem. Soc. Rev., 35, 237 (2006); doi:10.1039/b515269k.

K. Kaneda, K. Ebitani, T. Mizugaki and K. Mori, Bull. Chem. Soc. Jpn., 79, 981 (2006); doi:10.1246/bcsj.79.981.

M.D. Le Page and B.R. James, Chem. Commun., 1647 (2000); doi:10.1039/b005338o.

P. Phukan and A. Sudalai, Synth. Commun., 30, 2401 (2000); doi:10.1080/00397910008086882.

G.P. Boldrini, D. Savoia, E. Tagliavini, C. Trombini and A. Umani-Ronchi, J. Org. Chem., 50, 3082 (1985); doi:10.1021/jo00217a014.

T.T. Upadhya, S.P. Katdare, D.P. Sabde, V. Ramaswamy and A. Sudalai, Chem. Commun., 1119 (1997); doi:10.1039/a701518f.

S.K. Mohapatra, S.U. Sonavane, R.V. Jayaram and P. Selvam, Org. Lett., 4, 4297 (2002); doi:10.1021/ol026936p.

B.-C. Chen, J.E. Sundeen, P. Guo, M.S. Bednarz and R. Zhao, Tetrahedron Lett., 42, 1245 (2001); doi:10.1016/S0040-4039(00)02257-7.

T. Suwa, E. Sugiyama, I. Shibata and A. Baba, Synthesis, 789 (2000); doi:10.1055/s-2000-6273.

C.F. Lane, Synthesis, 135 (1975); doi:10.1055/s-1975-23685.

A.F. Abdel-Magid, K.G. Carson, B.D. Harris, C.A. Maryanoff and R.D. Shah, J. Org. Chem., 61, 3849 (1996); doi:10.1021/jo960057x.

M.D. Bomann, I.C. Guch and M.A. Dimare, J. Org. Chem., 60, 5995 (1995); doi:10.1021/jo00123a049.

A. Heydari, S. Khaksar, J. Akbari, M. Esfandyari, M. Pourayoubi and Tajbakhsh, Tetrahedron Lett., 48, 1135 (2007); doi:10.1016/j.tetlet.2006.12.069.

P.N. Rylabder, Hydrogenation Methods, Academic Press, New York (1985).

R.F. Borch, M.D. Bernstein and H.D. Durst, J. Am. Chem. Soc., 93, 2897 (1971); doi:10.1021/ja00741a013.

J.L. Luche, L. Rodriguza-Hahn and P. Crabbe, Chem. Commun., 601 (1978); doi:10.1039/c39780000601.

T. Kawakami, M. Miyatake, I. Shibata and A. Baba, J. Org. Chem., 61, 376 (1996); doi:10.1021/jo951500r.

J.C. Fuller, E.L. Stangeland, C.T. Goralski and B. Singaram, Tetrahedron Lett., 34, 257 (1993); doi:10.1016/S0040-4039(00)60561-0.

B.C. Ranu and A.R. Das, J. Org. Chem., 56, 4796 (1991); doi:10.1021/jo00015a042.

S.A. Khan, A.M. Asiri and K. Sharma, Med. Chem. Res., 22, 1998 (2013); doi:10.1007/s00044-012-0155-2.

A.M. Asiri and S.A. Khan, Molecules, 15, 4784 (2010); doi:10.3390/molecules15074784.

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Selective Reduction of a,b-Unsaturated Steroidal Carbonyl Compounds by NaBH4 in Presence of Guanidine Hydrochloride in Dioxane

Corresponding Author(s) : Salman Ahmad Khan

Abstract

Keywords

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