Hydrochloric Acid → HCID 59752202, compound

Participants

Reaction Steps

Sodium hydride (39 mg, 0.97 mmol) was added to a solution of 3-{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethyl-2-pyrrolidinone (214 mg, 0.880 mmol) in anhydrous tetrahydrofuran (6 mL) under nitrogen at 0° C. After 10 min, benzyl chloroformate (0.200 mL, 1.32 mmol) was added, and the mixture was allowed to warm to room temperature. After 24 h, the mixture was diluted with saturated aqueous sodium chloride (30 mL) and dichloromethane (30 mL). Hydrochloric acid (10 mL, 1 N) was then added, and the two phases were separated. The aqueous layer was extracted with dichloromethane (35 mL), and the dichloromethane layers were combined. After washing with saturated aqueous sodium chloride, they were dried over magnesium sulfate and concentrated to a tan oil, which was further purified by column chromatography on silica gel. Elution with 10:1 hexane:ethyl acetate afforded benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethyl-2-oxo-1-pyrrolidinecarboxylate as a colorless oil (312 mg, 94%). 1H NMR (300 MHz, DMSO-d6) δ 7.47-7.34 (m, 5H), 5.27 (1/2Abq, J=13 Hz, 1H), 5.21 (1/2Abq, J=13 Hz, 1H), 4.24 (s, 1H), 3.50 (1/2Abq, J=11 Hz, 1H), 3.38 (1/2Abq, J=11 Hz, 1H), 1.12 (s, 3H), 0.92 (s, 9H), 0.90 (s, 3H), 0.13 (s, 3H), 0.10 (s, 3H). ES-LCMS m/z 378 (M+H).

Provenance & Evidence