(2S,3RS)-2-(4-Bromophenoxy)-5-pyridin-3-ylpent-4-yn-3-ol → (2S,3RS)-2-(4-Bromophenoxy)-5-pyridin-3-ylpentan-3-ol

Participants

Reaction Steps

(2S,3RS)-2-(4-Bromophenoxy)-5-pyridin-3-ylpent-4-yn-3-ol (5.93 g, Example 15c)) was dissolved in ethyl acetate (100 ml) and hydrogenated at 5 atmospheres using 5% rhodium on charcoal (2.0 g) as catalyst. The mixture was filtered through Celite® and the filtrate concentrated under reduced pressure 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)-3-pentanol as the major diastereomer (3.21 g) and (2S,3S)-2-(4-bromophenoxy)-5-(pyridin-3-yl)-3-pentanol as the minor diastereomer (0.71 g).

Provenance & Evidence