(3Rs,4r)-4-(4-bromophenoxy)-1-pyridin-3-yl-pent-1-yn-3-ol → (3s,4r)-4-(4-Bromophenoxy)-1-pyridin-3-yl-pentan-3-ol

Participants

Reaction Steps

Prepared according to the method described in Example 1d) from (3RS,4R)-4-(4-bromophenoxy)-1-pyridin-3-yl-pent-1-yn-3-ol (5.93 g, Example 4c)) and 5% rhodium on charcoal (2.0 g) in ethyl acetate (100 ml) to give the sub-title compound as an oil and as a 4:1 mixture of diastereomers (5.6 g). The diastereomers were separated using normal-phase HPLC eluting with 3% isopropyl alcohol in dichloromethane to give (2S, 3R)-2-(4-bromophenoxy)-5-pyridin-3-yl-pentan-3-ol as the majordiastereomer (3.21 g) and (2S, 3S)-2-(4-bromophenoxy)-5-pyridin-3-yl-pentan-3-ol as the second eluting and minor diastereomer (0.71 g).

Provenance & Evidence