Sodium triacetoxyborohydride → (1R)-2-{[6-(But-3-ynyloxy)hexyl][(1S)-2-hydroxy-1-phenylethyl]amino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Participants

Reaction Steps

A mixture of 6-(but-3-ynyloxy)hexanal (434 mg) and (1R)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethanol (WO0196278 A2) (710 mg) in chloroform (10 ml) was treated at 20° C. with sodium triacetoxyborohydride (866 mg) and stirred under nitrogen for 2 days. The mixture was diluted with EtOAc and aqueous sodium bicarbonate solution. The organic phase was separated and washed with sodium bicarbonate solution, brine, dried and purified on a silica Bond Elut cartridge (10 g) eluting with dichloromethane, Et2O and finally EtOAc to give the title compound (810 mg): LCMS RT=2.69 min, ES+ve m/z 496 (M+H)+.

Provenance & Evidence