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Novel azaandrostane derivatives for the synthesis of 17β‐( N ‐ tert ‐butyl carbamoyl)‐4‐aza‐5α‐androst‐1‐ene‐3‐one
Author(s) -
Srinivasa Rao Divvela V. N.,
Trinadhachari Ganala Naga,
Prabahar Koilpillai Joseph,
Dandala Ramesh,
Sivakumaran Meenakshisundaram,
Naidu Andra
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440323
Subject(s) - chemistry , ene reaction , stereochemistry , androstane , medicinal chemistry
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).