Sodium borohydride → methyl 13-cyclohexyl-6-hydroxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

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Reaction Steps

Sodium borohydride (50 mg, 1.3 mmol) was added to a solution of methyl 13-cyclohexyl-6,7-dihydro-6-oxo-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (29 mg, 0.074 mmol) in methanol (4 mL) and tetrahydrofuran (2 mL) at rt. The evolution of H2 was instantaneous and stirring was continued for 30 min at rt. The mixture was concentrated on a rotary evaporator and and the residue purified on the Shimadzu preparative liquid chromatograph. The product containing fraction was concentrated on a Speed Vac® to leave the titled compound as a white solid (27.5 mg, 96%). ESI-MS m/z 390 (MH+); 1H NMR (500 MHz, CHLOROFORM-D) δ 1.18-1.31 (m, 1 H) 1.32-1.53 (m, 2 H) 1.60-1.70 (m, 1 H) 1.71-1.84 (m, 2 H) 1.86-2.18 (m, 4 H) 2.38-3.12 (m, 3 H) 3.36-3.83 (m, 1 H) 3.94 (m, 3 H) 4.39-4.68 (m, 2 H) 7.32-7.48 (m, 4 H) 7.76 (t, J=8.39 Hz, 1 H) 7.88 (t, J=8.09 Hz, 1 H) 8.14 (m, 1 H).

Provenance & Evidence