Aluminium lithium hydride → HCID 86591644, compound

Participants

Reaction Conditions

Reaction Steps

Trans-2-(5-cyano-1H-indol-3-yl)-cyclopentanecarboxylic acid methoxy-methyl-amide (460 mg, 1.5 mMol) was dissolved in THF and cooled to −40° C. Lithium aluminum hydride (117 mg, 3.1 mMol) was added and the temperature was maintained between −40 and −30° C. for 1 h. The reaction was quenched with ethyl acetate (10 mL) and warmed to 0° C. The reaction was treated dropwise with water (0.12 mL) and stirred 5 min. Then sodium hydroxide (1N, 0.36 mL) was added and the reaction was stirred 5 min. Then a further addition of water (0.12 mL) was made and the reaction was stirred for 20 min. The reaction was filtered through celite and sand, and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel with ethyl acetate/hexanes (50%) to give the product as a clear oil (252 mg, 68%). 1H NMR (400 MHz, CDCl3) δ 9.67 (1H, d, J=2.8 Hz), 8.37 (1H, brs), 7.96 (1H, s), 7.36–7.44 (2H, m), 7.14 (1H, d, J=2.3 Hz), 3.60 (1H, q, J=8.5 Hz), 2.98 (1H, q of d, J=7.5, 2.7 Hz), 2.30 (1H, m), 1.71–2.20 (5H, m); MS m/e 239.2 (M+H).

Provenance & Evidence