Borane → methyl 13-cyclohexyl-6-(hydroxymethyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

Participants

Reaction Steps

A solution of borane in THF (0.18 mL of 1 N, 0.18 mmol) was added to a solution of methyl (±)-6-carboxy-13-cyclohexyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (50 mg, 0.12 mmol) in THF (5 mL) at 0° C. The cooling bath was removed and stirring continued at ambient temperatures for 18 hr. The solution was diluted with ethyl acetate and washed with dilute HCl (1×), brine (3×), and then dried (Na2SO4). The crude product was 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 film (25 mg, 52%). ESI-MS m/z 404 (MH+); 1H NMR (300 MHz, MeOD) δ 1.14–2.19 (m, 11 H) 2.34–2.80 (m, 2 H) 2.82–3.26 (m, 2 H) 3.25–3.38 (m, 1 H) 3.44–3.82 (m, 1 H) 3.92 (s, 3 H) 4.48–4.61 (m, 1 H) 7.35–7.46 (m, 4 H) 7.68 (m, 1 H) 7.85 (m, 1 H) 8.17 (m, 1 H).

Provenance & Evidence