Dimethylamine → HCID 10015826, compound

Participants

Reaction Steps

Trans-3-(2-formyl-cyclopentyl)-1H-indole-5-carbonitrile (200 mg, 0.84 mMol) was stirred in THF (5 mL) and methanol (30 mL) with dimethylamine (0.84 mL, 2M in THF, 1.68 mMol) for 5 min. Sodium triacetoxyborohydride (530 mg, 2.52 mMol) was added and the reaction was stirred a further 30 min. The solvent was evaporated in vacuo and the residue was dissolved in 1N sodium hydroxide (20 mL). The reaction was extracted with ethyl acetate (3×10 mL), dried with magnesium sulfate, and evaporated to a white powder. The material was purified by precipitation from hot methylene chloride to provide the product (144 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 8.32 (1H, brs), 8.00 (1H, s), 7.39 (2H, m), 7.12 (1H, d, J=1.8 Hz), 2.90 (1H, m), 2.17 (6H, s), 2.06–2.33 (5H, m), 1.66–1.90 (3H, m), 1.49 (1H, m); MS m/e 268.2 (M+H).

Provenance & Evidence