Acetic Acid → 3-[10-bromo-2-(trifluoromethyl)-5,6,8,9-tetrahydro-7H-[1,3]oxazolo[4,5-h][3]benzazepin-7-yl]-1-butanol

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Reaction Steps

A mixture of 10-bromo-2-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-[1,3]oxazolo[4,5-h][3]benzazepine (250 mg, 1 eq), 4-hydroxy-butan-2-one (0.077 ml, 1.2 eq), acetic acid (0.042 ml, 1 eq) and sodium triacetoxyborohydride (314 mg, 2 eq) in THF (2.5 ml) was stirred at room temperature for 20 hours. Additional 4-hydroxy-butan-2-one (0.24 eq) and sodium triacetoxyborohydride (0.4 eq) were added and the mixture was stirred for 5 hours. Then, the mixture was diluted with DCM and washed with 5% NaHCO3 and brine. The organic phase was dried (Na2SO4) and concentrated. The crude was purified on silica gel (DCM/MeOH/conc.NH4OH, 100/2.5/0.25) providing the title compound (218 mg, 72% yield).

Provenance & Evidence