Effect of solvent on stereoselectivity in Pd/C (Type 39K)-catalyzed hydrogenation of methyl 3-oxo-4-aza-5-androstene-17-carboxylate, a key intermediate for finasteride and dutasteride

Organic Process Research and Development

Volumn 11, Issue 5, 2007, Pages 889-891

  Karrothu, Srihari Babu ^a   Kolla, Naveenkumar ^a   Lekkala, Amarnath Reddy ^a   Golla, China Malakondaiah ^a   Anand, Ramasamy Vijaya ^a   Gandu, Venkateswarlu ^b   Bhattacharya, Apurba ^a   Padi, Pratap Reddy ^a   Bandichhor, Rakeshwar ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

^b OSMANIA UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35348891690     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op700104f     Document Type: Article

References (14)

1. Amory, John K.; Page, Stephanie T.; Bremner, William J. Center for Research in Reproduction and Contraception, Divisions of General Internal Medicine and Endocrinology, Metabolism and Nutrition, Department of Medicine, University of Washington Medical School, Seattle, Washington.
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5. Gary, H. R.; David, B., R.; Johnston, N. J.; Warren, N. J.; Glen, E. A., U.S. Patent 4,377,584, 1983.
6. (a) Kan, W. M.; Yek, Y. L.; Wang, Y.-H.; Chern, C-Y. Chin. Pharma. J. 2003, 55, 213-219.
7. (b) Miller, R. A.; Humphrey, G. R.; Thompson, A. S. Tetrahedron Lett. 1995, 36, 7949-7952.
8. (c) Roman, D.; Alan, M.; Jeffrey, T.S. U.S. Patent 6,794,508B2, 2004.
9. (a) www.matthey.com/about/preciousmetal.htm.
10. (b) The other palladium on carbon was procured from Hindustan Platinum Limited.
11. There are three types of catalysts which were screened for this hydrogenation reaction beside type 39. No reduction was observed using types 5T487, 5T490, or 5T58.
12. The compounds of 2 and 7 are soluble in minimum quantities of acetic acid (Table 2). Hence, acetic acid is directly used as a cosolvent along with methanol during the optimization of solvent quantity.
13. 2, manufactured by Chemee Equipment Pvt. Ltd., Mumbai, India, was used for the reaction.
14. 18, 250 mm × 4.6 mm, 5 μm. Mobile phase (MP): MP-A, 100% buffer (0.5 g of o-phosphoric acid in 1000 mL of water); MP-B, acetonitrile and water in the ratio of 70:30; 0.8 mL/min; 210 nm. See Table 3 for the gradient profile.