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

Temperature

-63 °C

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

1. stirringThe reaction mixture was stirred for 20 min at −63° C
2. temperatureThe solution was warmed to −35° C.
3. temperatureimmediately cooled to −63° C
4. stirringIt was stirred at this temp
5. waitfor 1 h
6. temperatureThe reaction mixture was warmed to 10° C.
7. washwashed with water (2×200 mL)
8. dry with materialphase was dried over magnesium sulfate
9. customThe solvent was removed in vacuo

ORD record

ord-800706b6959041468da8a33f76b33011

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350767B1