Dimethyl Sulfoxide → tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of oxalyl chloride (90 mL, 1.03 mol) in CH2Cl2 was added dropwise a solution of DMSO (100 mL, 1.41 mol) in CH2Cl2. The mixture was stirred at −78° C. for 1 hr, and a solution of (R)-tert-butyl 1-hydroxypropan-2-ylcarbamate (90 g, 0.51 mol) in CH2Cl2 was added. After stirring for 3 hr, 500 mL of triethylamine was added and the reaction mixture was stirred for another 3 h at −78° C. The reaction was quenched with 1% HCl and the reaction mixture was warmed to RT. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The organic layer was washed with water, dried over MgSO4, and evaporated to provide crude N.1, (R)-tert-butyl 1-oxopropan-2-ylcarbamate (76.0 g, 85.4%). 1H NMR (CDCl3) δ 9.56 (s, 1H), 4.23 (br s, 1H), 1.45 (s, 9H), 1.32 (s, 3H).

Provenance & Evidence