Dimethyl Sulfoxide → HCID 57451421, compound

Participants

Reaction Conditions

Reaction Steps

A solution of oxalyl chloride (15.24 g, 120 mmol) in 200 mL of MeCl2 was stirred and cooled to −60° C. followed by the drop wise addition of dimethylsulfoxide (19.7 g, 252 mmol) in 60 ml of MeCl2. After 10 min, a solution of 2-Boc-amino-2-methyl-1-propanol (18.9 g, 100 mmol) in MeCl2 (60 ml) was added drop wise at −70° C. The reaction mixture was allowed to warm to −40° C. for 10 min followed by cooling to −70° C. before the addition of a solution of triethylamine (28.28 g, 280 mmol) in MeCl2 (60 mL). The reaction mixture was allowed to warm to room temperature over a two-hour period and 40 mL of saturated sodium dihydrogen phosphate was added. The organic layer was washed with brine and dried over MgSO4. The solvent was removed to yield 17.3 g of 2-Boc-amino-2-methylpropionaldehyde.

Provenance & Evidence