(3s, 4s)-4-(4-Bromophenoxy)-5-(methyl)-1-pyridin-3-yl-3-hexanol → (3RS, 4S)-4-(4-Bromophenoxy)-5-(methyl)-1-pyridin-3-yl-3-hexanol

Participants

Reaction Steps

(3RS, 4S)-4-(4-Bromophenoxy)-5-(methyl)-1-pyridin-3-yl-hex-1-yn-3-ol (13.6 g) was dissolved in ethyl acetate (350 ml) and hydrogenated at 3 atmospheres for 6 days using 10% rhodium on charcoal (2.1 g) as catalyst. The catalyst and solvent were replaced 5 times during this period. The mixture was filtered through Celite® and the filtrate concentrated under reduced pressure to give a. The mixture was purified by HPLC eluting with dichoromethane:2-propanol (97:3) to give a mixed fraction containing reduced and unreduced (6.0 g), pure (3S, 4S)-4-(4-bromophenoxy)-5-(methyl)-1-pyridin-3-yl-3-hexanol (1.73 g) and pure (3R,4S)-4-(4-bromophenoxy)-5-(methyl)-1-pyridin-3-yl-3-hexanol (2.73 g).

Provenance & Evidence