Asymmetric Hydrolysis of (±)-1,2-Diacetoxy-3-chloropropane and Its Related Compounds with Lipase. Synthesis of Optically Pure (S)-Propranolol

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Abstract
Asymmetric hydrolysis of (±)-1,2-diacetoxy-3-chloropropane (1) with a very small amount of a lipoprotein lipase gave (S)-1 of 90% enantiomeric excess (e.e.). Reactions of (S)-1 with phenols in an alkaline condition yielded the corresponding (S)-3-aryloxy-1,2-propanediols. From (S)-3-(1-naphthoxy)-1,2-propanediol (5) was synthesized the optically pure (S)-isomer of propranolol [1-isopropylamino-3-(1-naphthoxy)-2-propanol] (9), one of the ²-adrenergic blocking agents. Hydrolysis of (±)-1,2-diacetoxy-3-bromopropane (11) and (±)-1,2-diacetoxyethylbenzene (12) with the lipase afforded (S)-11 of 77% e.e. and (R)-12 of 73% e.e., respectively.