Dimethyl Sulfoxide → tert-Butyl N-(3-oxopropyl)carbamate

Temperature

-70 °C

A solution of oxalyl dichloride (597 μl) in dry dichloromethane (7 ml) was cooled to −70° C. in nitrogen atmosphere, and a solution of dimethylsulfoxide (1.15 ml) in dry dichloromethane (1.5 ml) was added slowly and stirred for 30 minutes at −70° C. To the reaction mixture was added a solution of (3-hydroxypropyl)carbamic acid tert-butyl ester (1.0 g) in dry dichloromethane (7 ml) slowly to maintain the reaction temperature at −60° C. and stirred for 30 minutes at −70° C. To the reaction mixture was added triethylamine (3.98 ml) slowly to maintain the reaction temperature at −60° C. Then the reaction mixture was allowed to warm to room temperature. To the reaction mixture was added water (10 ml) and stirred for 10 minutes, then the organic layer was separated. The aqueous layer was extracted with dichloromethane (50 ml×2). The organic layer was combined and washed with brine, dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 3-tert-butoxycarbonylaminopropionaldehyde (1.28 g), that was used crude in the next reaction.

1. temperatureto maintain the reaction temperature at −60° C.
2. stirringstirred for 30 minutes at −70° C
3. temperatureto maintain the reaction temperature at −60° C
4. temperatureto warm to room temperature
5. stirringstirred for 10 minutes
6. customthe organic layer was separated
7. extractionThe aqueous layer was extracted with dichloromethane (50 ml×2)
8. washwashed with brine
9. dry with materialdried over magnesium sulfate
10. filtrationMagnesium sulfate was filtered off
11. customthe filtrate was evaporated under reduced pressure

ORD record

ord-87ae0ba96de641739282a2da9670b797

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884868B1