Sodium cyanoborohydride → HCID 22609198, compound

Participants

Reaction Steps

NaCNBH3 (0.223 g, 3.54 mmol) was added to a solution of 10-(2,6-difluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.336 g, 1.13 mmol) in CF3CO2H (6 mL), which was cooled in an ice-water bath. After stirring for 4 h, the reaction mixture was quenched by adding 6N HCl (6 mL). The resulting mixture was refluxed for 0.45 h. The mixture was cooled and made basic by the addition of 6N NaOH (25 mL). The basic mixture was combined with CHCl3 (30 mL) and H2O (5 mL) and the layers were separated. The aqueous layer was extracted with CHCl3 (2×50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product (0.78 g) was chromatographed (SiO2 35 g, eluted with 90:10:2 CH2Cl2:CH3OH:conc. NH4OH) to yield 10-(2,6-difluorophenyl)-1,2,3,4,5,5a,6,10b-octahydroazepino[4,5-b]indole (0.232 g) in 69% yield. 1H NMR (400 MHz, CD3OD) δ 1.37, 1.61, 1.94, 2.05, 2.44, 2.65-2.73, 3.05, 3.54, 4.19, 6.52, 6.63, 7.03-7.09, 7.41: MS (ESI+) for C18H18F2N2 m/z 301.2 (M+H)+.

Provenance & Evidence