Aluminium lithium hydride → HCID 57794729, compound

Participants

Reaction Conditions

Reaction Steps

To 16.2 mL 1M lithium aluminum hydride (16.2 mmol) in diethyl ether at 0° C. (1S,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropanecarbonitrile (4.25 g, 16.2 mmol), accessed via the method of Preparation 3A, dissolved in 17 mL diethyl ether. After complete addition, the reaction mixture was stirred at 0° C. for 2 h followed by 4 h at ambient temperature. The reaction mixture was diluted with 360 mL diethyl ether and quenched with successive addition of 0.6 mL water, 0.6 mL 15% NaOH, and 3.0 mL water. The reaction mixture was filtered and the filtrate was concentrated to a clear oil. The oil was purified by flash chromatography (SiO2, 3→5% CH3OH/EtOAc with 1% NH4OH) to give the title product (3.08 g, 11.5 mmol, 71%) as a single diastereomer. 1H NMR (300 MHz, CDCl3) δ 7.37-7.19 (m, 10H), 4.62-4.54 (m, 2H), 3.88 (m, 1H), 3.34 (m, 1H), 2.96 (d, J=14.1 Hz, 1H), 2.70 (d, J=14.1 Hz, 1H), 1.58 (m, 1H), 1.00 (m, 1H), 0.62 (m, 1H). ES-LCMS m/z 268.4 (M+H).

Provenance & Evidence