Dimethyl Sulfoxide → HCID 23053108, compound

Participants

Reaction Steps

To a −50 to −60° C. cooled solution of oxalyl chloride (5.3 mL of a 2 M solution in methylene chloride, 10.6 mmol) in methylene chloride (5.3 mL) was added methyl sulfoxide (1.5 mL, 21.2 mmol) in methylene chloride (5 mL). After 3 min, a solution of 1-(3-methoxybenzyl)pyrrolidin-3-ol (2.0 g, 9.6 mmol) from Step A above in methylene chloride (10 mL) was added dropwise. After 25 min added triethylamine (6.8 mL, 4.8 mmol) and the reaction mixture was warmed to ambient temperature. Water (30 mL) was added and the aqueous layer was separated and extracted with methylene chloride (20 mL). The combined organic layers were dried over 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 (1.3 g, 66%) as a colorless oil: 1H NMR (DMSO-d6, 300 MHz) δ 7.24 (dd, J=8.1, 8.1 Hz, 1H), 6.91-6.81 (m, 3H), 3.74 (s, 3H), 3.65 (s, 2H), 2.87-2.82 (m, 4H), 2.37-2.32 (m, 2H).

Provenance & Evidence