J. Xian
2009
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Journal
Journal of Shenyang Pharmaceutical University
Abstract
Objective To prepare(R)-5-(1-hydroxyl-2-bromoethyl)salamide acetate.Methods 5-Bromoacetyl salamide acetate(7)was synthesized by using salicylic acid as starting material via a five steps process including esterification,ammonolysis,Friedel-Crafts acylation,α-bromination and acetylation.Compound 7 was subjected to transfer hydrogenation with chiral catalyst(S,S)-Ru-N-monosulfonated-1,2-diphenylethanediamine((S,S)-Ru-TsDPEN)to afford the target compound.Results The desired product is synthesized in the overall yield of 31.5%.The chiral catalyst(S,S)-Ru-TsDPEN shows good catalytic activity and enantioselectivity in transfer hydrogenation of compound 7 with 80.8% enantiomeric excess.Conclusions (R)-5-(1-hydroxyl-2-bromoethyl)salamide acetate,which is a key chiral intermediate of labetalol,was synthesized by using chiral catalyst(S,S)-Ru-TsDPEN in transfer hydrogenation so as to lay a foundation for further study on synthesis of labetalol.