Benzylamine → (R)-3-Benzylamino-1,1,1-trifluoro-propan-2-ol

Participants

Reaction Steps

To a solution of lithium trifluoromethanesulfonate (1.43 g, 9.17 mmol) in CH3CN (30 ml) was added (R)-(+)-3,3,3-trifluoro-1,2-epoxypropane (10.77 g, 96 mmol) slowly at −10° C. After 5 minutes benzylamine (10 ml, 92 mmol) was added slowly. The mixture was allowed to warm as the bath warmed to rt overnight. The mixture was concentrated. The crude product was subjected to silica gel chromatography (330 g, 0-50% EtOAc/hexanes, 10 minute gradient) to afford (R)-3-(benzylamino)-1,1,1-trifluoropropan-2-ol (4-2, 15.9 g, 79%) as a white solid. LRMS m/z (M+H)+ 220.2 calc. 220.1 found.

Provenance & Evidence