Water → HCID 118415299, compound

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (2.3 g, 61.0 mmol, 1.5 eq) in anhydrous THF (200 mL) at 0° C. was added (S)-2-(benzyl(methyl)amino)-2-cyclopentylacetic acid (3) (10.0 g, 40.0 mmol, 1.0 eq) in portions at 0° C. The reaction mixture was stirred at room temperature for 2 h followed by heating to reflux for 2 h, After cooled, water (2.5 mL) was added at 0° C. followed by 5% NaOH (2.5 mL, aq). The suspension formed was filtered and washed with ethyl acetate (50 mL). Water (250 mL) was then added to the filtrate, which was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulphate and evaporated in vacuo to give the product 4 as an oil (quant); LC-MS: m/z 234 [M+H+]+

Provenance & Evidence