Dimethyl Sulfoxide → tert-butyl N-methyl-N-(3-oxopropyl)carbamate

Temperature

-78 °C

Dimethylsulfoxide (6.22 ml, 87.6 mmol) was dissolved in dry dichloromethane (100 ml) under nitrogen and the solution was cooled to −78° C. with stirring. Oxalyl chloride (3.95 ml, 45.4 mmol) was then added dropwise and the solution was stirred at −78° C. for a further 30 minutes when effervescence had ceased. A solution of 1,1-dimethylethyl (3-hydroxypropyl)methylcarbamate (6.62 g, 35.0 mmol) in dichloromethane (100 ml) was then added dropwise at −78° C. The resultant solution was stirred at −78° C. for 45 minutes, then a solution of methylamine (24.4 ml, 175 mmol) in dichloromethane (50 ml) was added. The resultant solution was allowed to warm to room temperature and stirred for a further 18 h. The reaction mixture was then poured into brine and extracted with dichloromethane three times. The combined organic fractions were then washed with brine, dried (MgSO4) and evaporated. The residue was triturated with diethyl ether and filtered. The solvent was evaporated to give the title compound (6.60 g, 100%) as an orange oil.

1. stirringthe solution was stirred at −78° C. for a further 30 minutes when effervescence
2. temperatureto warm to room temperature
3. stirringstirred for a further 18 h
4. extractionextracted with dichloromethane three times
5. washThe combined organic fractions were then washed with brine
6. dry with materialdried (MgSO4)
7. customevaporated
8. customThe residue was triturated with diethyl ether
9. filtrationfiltered
10. customThe solvent was evaporated

ORD record

ord-4152c0668aed43b79771701125461947

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119109B2