Dichloromethane → 2-Bromomethylnaphthalene

Participants

Reaction Steps

In an analogous manner to that described in Example 71(a)-(b), from benzyl rac-3-aza-7-oxa-bicyclo[4.1.0]heptane-3-carboxylate by reaction with 4-bromophenol there was obtained (3RS,4RS)-1-[4-(4-bromo-phenoxy)-3-hydroxy-piperidin-1-yl]-2-phenyl-ethanone as a colourless solid [Rf : 0.40 (SiO2, methylene chloride:ethyl acetate=2:1)], alkylation of which with 2-bromomethylnaphthalene gave benzyl (3RS,4RS)-4-(4-bromo-phenyl)-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless solid; MS: 454, 456 (M-benzyl)+.

Provenance & Evidence