Tetrahydrofuran → HCID 59752197, compound

Participants

Reaction Steps

A solution of tetrabutylammonium fluoride in anhydrous tetrahydrofuran (1.1 mL, 1M, 1.1 mmol) was added to a solution of 3-{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethyl-2-oxo-1-pyrrolidinecarboxylate (202 mg, 0.54 mmol) in anhydrous tetrahydrofuran (2 mL) under nitrogen. After 45 min, the reaction mixture was subjected directly to column chromatography. Elution with 50% ethyl acetate in hexane afforded benzyl 3-hydroxy-4,4-dimethyl-2-oxo-1-pyrrolidinecarboxylate as an oil that solidified upon standing (133 mg, 94%). 1H NMR (300 MHz, DMSO-d6) δ 7.47-7.36 (m, 1H), 5.88 (d, J=6 Hz, 1H), 5.24 (s, 2H), 3.99 (d, J=6 Hz, 1H), 3.48 (1/2Abq, J=10 Hz, 1H), 3.35 (1/2Abq, J=10 Hz, 1H), 1.11 (s, 3H), 0.89 (s, 3H). ES-LCMS m/z 378 (M+H).

Provenance & Evidence