Dimethyl Sulfoxide → HCID 83854681, compound

Participants

Reaction Conditions

Reaction Steps

Dimethyl sulfoxide (0.252 mL, 3.55 mmol) was added to a to −78° C. solution of oxalyl chloride (0.200 mL, 2.37 mmol) in methylene chloride (5.4 mL). After 10 min, a solution of tert-butyl 4-benzyl-3-(hydroxymethyl)piperazine-1-carboxylate (0.63 g, 2.0 mmol from Step 1) in methylene chloride (2.8 mL) was slowly introduced over 15 min. After stirring at −78° C. for 1 h, triethylamine (1.38 mL, 9.87 mmol) was added. The mixture was warmed to RT over 30 min and then stirred for another 30 min at that temperature. The reaction mixture was diluted with DCM, washed with water (twice) and brine (once), dried over sodium sulfate, decanted and concentrated to give product as a light yellow oil (570 mg, 95%). 1H NMR (300 MHz, CDCl3): δ 9.67 (d, 1H), 7.36-7.24 (m, 5H), 3.89 (d, 1H), 3.65 (dd, 1H), 3.57 (d, 1H), 3.57-3.45 (br m, 2H), 3.36-3.22 (br m, 1H), 3.10-2.98 (br m, 1H), 2.93 (ddd, 1H), 2.30 (ddd, 1H), 1.45 (s, 9H); LCMS (M+H)+: 305.0.

Provenance & Evidence