Dimethyl Sulfoxide → HCID 23053108, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (14.6 mL, 170 mmol) in methylene chloride (100 mL) at −78° C., was added dimethyl sulfoxide (14.3 mL, 170 mmol). After 15 min, a solution of 1-(3-methoxybenzyl)pyrrolidin-3-ol (11.8 g, 56.8 mmol) from Step A above in methylene chloride (100 mL) was added dropwise. After 4 h, triethylamine (52 mL, 369 mmol) was added and the reaction mixture was warmed to ambient temperature. Water (50 mL) was added and the aqueous layer was separated and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (methylene chloride to 1:1 methylene chloride/ethyl acetate) to provide 1-(3-methoxybenzyl)pyrrolidin-3-one (8.0 g, 68%) as a colorless oil: 1H NMR (CD3OD, 400 MHz) δ 7.26 (t, J=7.9 Hz, 1H), 7.00-6.92 (m, 2H), 6.89-6.81 (m, 1H), 3.81 (s, 3H), 3.72 (s, 2H), 2.99-2.95 (m, 2H), 2.94 (s, 2H), 2.41 (t, J=7.0 Hz, 2H); ESI MS (m/z) 206 [M+H]+.

Provenance & Evidence