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Synthesis of naproxen via regioselective ring opening of (2 S ,3 S )‐epoxy‐1‐butanol
Author(s) -
Ahn Kyo Han,
Jin Chang Soo,
Ho Kang Dong,
Shin Yong Soon,
Kim Jeong Sook,
Han Do Soon,
Kim Dong H.
Publication year - 1993
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.5570300337
Subject(s) - chemistry , potassium permanganate , epoxide , regioselectivity , stereospecificity , epoxy , diol , sodium periodate , butanol , ring (chemistry) , enantiomer , alcohol , organic chemistry , potassium , medicinal chemistry , nuclear chemistry , ethanol , catalysis
Abstract (S)‐Naproxen was synthesized by the regioselective and stereospecific epoxide ring opening of (2 S ,3 S )‐epoxy‐1‐butanol (2) with diethyl‐2‐(6‐methoxynaphthyl)aluminium (5) as the key step. Thus, treatment of di‐ethylaluminate of 2 with 5 at 0° afforded (2 S ,3 S )‐3‐(6‐methoxy‐2‐naphthyl)butan‐1,2‐diol (6) , which was oxidized by sequential treatment with sodium periodate and potassium permanganate in a mixture of tert ‐butyl‐alcohol and phosphate buffer ( p H 7.0) to give naproxen in high enantiomeric purity.