P-Hydroxynorephedrine → ethyl 2-[2-bromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetate

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Reaction Steps

A suspension of (1R,2S)-2-amino-1-(4-hydroxyphenyl)propan-1-ol (475 mg), ethyl 2-[2-bromo-4-(2-bromoethyl)phenoxy]acetate (520 mg) and molecular sieves 4A powder (1.42 g) in N,N-dimethylformamide (4.7 ml) was stirred for 2 days at room temperature. Purification of the reaction mixture by medium pressure liquid column chromatography on aminopropyl silica gel (eluent:dichloromethane/methanol=10/1) gave ethyl 2-[2-bromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetate (356 mg).

Provenance & Evidence