Dimethyl Sulfoxide → HCID 58180954, compound

Participants

Reaction Steps

Dimethyl sulfoxide (0.732 mL, 10.3 mmol) was added to a solution of oxalyl chloride (0.582 mL, 6.88 mmol) in DCM (13 mL) at −78° C. After stirring for 10 minutes, tert-butyl (3R)-4-(2-hydroxyethyl)-3-methylpiperazine-1-carboxylate (1.4 g, 5.7 mmol) in DCM (6.6 mL) was added over 15 minutes. The reaction was stirred at −78° C. for 1 hour, then triethylamine (3.99 mL, 28.6 mmol) was added. The reaction was stirred, with warming to room temperature, for 1 hour. The reaction mixture was diluted with DCM, washed twice with water and once with brine, dried over sodium sulfate and concentrated to afford product, used without further purification (1.20 g, 86%). 1H NMR (300 MHz, CDCl3): δ 9.72 (t, 1H), 3.90-3.65 (m, 2H), 3.43 (d, 1H), 3.15 (ddd, 1H), 3.04 (dd, 1H), 2.89-2.67 (m, 2H), 2.52-2.34 (m, 2H), 1.46 (s, 9H), 1.02 (d, 3H); LCMS (M+H2O+H)+: 261.2.

Provenance & Evidence