Dimethyl Sulfoxide → HCID 53685202, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (2.0M in methylene chloride, 9.60 mL, 19.2 mmol) in methylene chloride (100 mL) at −60° C. was added a solution of dimethyl sulfoxide (3.01 g, 38.6 mmol) in methylene chloride (10 mL) and the mixture was stirred for 5 min. A solution of (S)-(−)-1-(t-butoxycarbonyl)-2-pyrrolidinemethanol (3.08 g, 15.3 mmol) in methylene chloride (20 mL) was added dropwise over 5 min. After 30 min, triethylamine (12.8 mL, 91.8 mmol) was added and the reaction mixture was stirred at −60° C. for 15 min and then warmed to rt for a further 10 min. Water (50 mL) was added and the mixture extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The crude residue was dissolved in methylene chloride (100 mL) and treated with methyl (triphenylphosphoranylidene)acetate (1.4 eq). After 15 h the reaction mixture was concentrated and purified by silica gel chromatography to give the desired product (3.54 g, 90%).

Provenance & Evidence