Aluminium lithium hydride → HCID 57794732, compound

Participants

Reaction Conditions

Reaction Steps

To 19.4 mL IM lithium aluminum hydride (19.4 mmol) in diethyl ether at 0° C. was added (1R,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropanecarbonitrile (5.10 g, 19.4 mmol), accessed via the method of Preparation 3B, dissolved in 20 mL diethyl ether. After complete addition, the reaction mixture was stirred at 0° C. for 3 h. 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→7% CH3OH/EtOAc with 1% NH4OH) to give the title product (3.03 g, 11.3 mmol, 59%) as a single diastereomer. 1H NMR (300 MHz, CDCl3) δ 7.35-7.21 (m, 10H), 4.35-4.25 (m, 2H), 3.22-3.18 (m, 1H), 3.00-2.94 (m, 2H), 2.43 (d, J=13.5 Hz, 1H), 1.36 (m, 1H), 0.91 (m, 1H), 0.78 (m, 1H). ES-LCMS m/z 268.4 (M+H).

Provenance & Evidence