Acetic Acid → N-((1R)-1-formyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (4.24 mL, 48.61 mmol) was dissolved in dichloromethane (30 mL). The solution was cooled to -63° C. A solution of DMSO (4.6 mL, 64.81 mmol) in dichloromethane (20 mL) was added dropwise. The solution was stirred for 5 min and a solution of N-((1R)-1-(hydroxymethyl)-2-phenylethyl)-N-methylcarbamic acid tert-butylester (8.6 g, 32.41 mmol) in dichloromethane (200 mL) was added dropwise over a period of 30 min. The reaction mixture was stirred for 20 min at -63° C. A solution of triethylamine (18.07 mL, 129.62 mmol) in dichloromethane (40 mL) was added over a period of 25 min. The solution was warmed to -35° C. and immediately cooled to -63° C. It was stirred at this temp. for 1 h. Acetic acid (8.15 mL, 142.58 mmol) was added. The reaction mixture was warmed to 10° C. and washed with water (2×200 mL) and satd. sodium hydrogencarbonate solution (150 mL). The org. phase was dried over magnesium sulfate. The solvent was removed in vacuo to give 7.536 of N-((1R)-1-formyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester.

Provenance & Evidence