Novel azaandrostane derivatives for the synthesis of 17β-(N-tert-butyl carbamoyl)-4-aza-5α-androst-1-ene-3-one

✍ Scribed by Divvela V. N. Srinivasa Rao; Ganala Naga Trinadhachari; Koilpillai Joseph Prabahar; Ramesh Dandala; Meenakshisundaram Sivakumaran; Andra Naidu

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2007
• Tongue: English
• Weight: 297 KB
• Volume: 44
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570440323

✦ Synopsis

Abstract

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A new industrially viable process for the preparation of 1β‐(N‐tert‐butyl carbamoyl)‐4‐aza‐5α‐androst‐1‐ene‐3‐one, also known by the generic name finasteride (6) from the new azaandrostane derivatives such as 1β‐(N‐tert‐butyl carbamoyl)‐4‐benzoyl‐4‐aza‐5α‐androstane‐3‐one (4), 1β‐(N‐tert‐butyl carbamoyl)‐4‐benzoyl‐4‐aza‐5α‐androst‐1‐ene‐3‐one (5) is reported. In this process, benzoyl group is demonstrated as a novel protecting group for lactamic NH group. The structures of newly prepared compounds were established on the basis of spectral data (IR, ^1^H‐NMR, and MS).