An enantioselective synthesis of S-γ-[(4-trifluoromethyl)phenoxy]benzenepropanamine-[3-14C] hydrochloride, an important metabolite of fluoxetine hydrochloride

✍ Scribed by William J. Wheeler

• Book ID: 102375967
• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: French
• Weight: 472 KB
• Volume: 31
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580310608

✦ Synopsis

Abstract

The S‐enantiomer of γ‐[(4‐trifluoromethyl)phenoxy]benzenepropanamine‐[3‐^14^C] hydrochloride has been prepared in eight steps from acetophenone‐[carbonyl‐^14^C]. The key step in the synthesis involved the enantioselective reduction of R‐2‐chloroacetophenone‐[1‐^14^C] with (‐)‐diisopinocampheylchloroborane in an 86.5% yield. The chlorohydrin was converted to R‐phenyloxirane‐[1‐^14^C], which was subsequently converted to the corresponding R‐cyanohydrin by reaction with TMS‐CN/CaO. Borane reduction and arylation, followed by salt formation yielded S‐γ‐[(4‐trifluoromethyl)phenoxy]benzenepropanamine‐[3‐^14^C] hydrochloride.