Sodium hydride → 1-Azetidinecarboxylic acid, 3-(2-oxo-1-pyrrolidinyl)-, 1,1-dimethylethyl ester

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Reaction Steps

A solution of 3-(4-chlorobutyrylamino)azetidine-1-carboxylic acid tert-butyl ester (1.04 g, 3.76 mmol) in DMF (15 mL) was cooled to 0° C. before the addition of NaH (180 mg, 4.51 mmol). The resulting mixture was allowed to stir for 2 h then quenched with H2O and extracted with EtOAc. The organic phase was washed with H2O and brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, EtOAc:cyclohexane, 20-100%) affording 3-(2-Oxopyrrolidin-1-yl)azetidine-1-carboxylic acid tert-butyl ester as a brown oil (320 mg, 35%). 1H NMR (CDCl3, 300 MHz): δ 4.99 (m, 1 H), 4.15 (m, 2 H), 3.97 (m, 2 H), 3.57 (t, J=7.0 Hz, 2 H), 2.42 (t, J=8.1 Hz, 2 H), 2.15-2.02 (m, 2 H) and 1.45 (s, 9 H)

Provenance & Evidence