Sodium cyanoborohydride → HCID 69894679, compound

Participants

Reaction Steps

A 0° C. solution of 10-(2-methoxyphenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole hydrochloride from above (286 mg, 0.87 mmol) in trifluoroacetic acid (4 mL) was treated with a solution of sodium cyanoborohydride (278 mg 4.42 mmol) in methanol (1 mL). The reaction was allowed to slowly warm to room temperature over 3.8 hours then diluted with water and concentrated in vacuo to remove the majority of acid. The residue was made basic with 15% NaOH, extracted with CH2Cl2 dried over MgSO4 and concentrated in vacuo and passed through a column of silica gel with 1:19 methanol/chloroform with 1% NH4OH to give 91 mg (36%) of a white foam as the title compound: 1H NMR (400 MHz, Acetone-d6) δ 7.34-7.30 (m, 1 H), 7.17 (dd, J=7.4 Hz, 1.7 Hz, 1 H), 7.06 (d, J=8.3 Hz, 1 H), 7.00-6.92 (m, 2 H), 6.47 (d, J=7.7 Hz, 1 H), 6.42 (d, J=7.6 Hz, 1 H), 4.90 (br s, 1 H), 4.19-4.14 (m, 1 H), 3.78 (s, 3 H), 3.65-3.60 (m, 1 H), 2.97-2.93 (m, 1 H), 2.64-2.56 (m, 2 H) 2.35-2.29 (m, 1 H), 1.98-1.94 (m, 1 H), 1.48-1.44 (m, 1 H), 1.28-1.23 (m, 1 H); HRMS (FAB) calcd for C19H22N2O1+H1 295.1810, found 295.1798.

Provenance & Evidence