Dimethyl Sulfoxide → HCID 86625742, compound

Participants

Reaction Steps

To a solution of DMSO (5.11 mL, 72.1 mmol) in CH2Cl2 (25 mL) at −78° C. was added a solution of oxalyl chloride (3.15 mL, 36.0 mmol) in CH2Cl2 (25 mL) dropwise. After 10 min of additional stirring, a solution of 1-benzyl 2-methyl (2R)-2-(3-hydroxypropyl)pyrrolidine-1,2-dicarboxylate [Cox and Lectka (1998) J. Am. Chem. Soc. 120, 10660-10668] (7.72 g, 24.0 mmol) in CH2Cl2 (50 mL) at −78° C. was added dropwise. After stirring for an additional 1 h, triethylamine (16.7 mL, 120 mmol) was added slowly. The reaction mixture was stirred for 1 h at −78° C. and 2.5 h at ambient temperature. Water (100 mL) was added slowly and the quenched mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were washed with 10% HCl (50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—90:10 to 0:100, to give the title compound. MS: m/z=320 (M+1).

Provenance & Evidence