(3RS, 4S)-4-(4-Bromophenoxy)-1-pyridin-3-yl-hex-1-yn-3-ol → (3r,4s)-4-(4-Bromophenoxy)-1-pyridin-3-yl-hexan-3-ol

Participants

Reaction Steps

Prepared according to the method described in Example 1d) from (3RS,4S)-4-(4-bromophenoxy)-1-pyridin-3-yl-hex-1-yn-3-ol (3.42 g, Example 87c)) and 5% rhodium on carbon (0.5 g) in ethyl acetate (100 ml). After work up crude material was purified by flash column chromatography over silica eluting with ethyl acetate to give a mixture of diastereomers. The mixture was separated by normal-phase HPLC eluting with 2% propan-2-ol in dichloromethane to give the sub-title compound as the second eluting, major diastereomer (2 g).

Provenance & Evidence