Dimethyl Sulfoxide → Tert-butyl 3-oxopyrrolidine-1-carboxylate

Temperature

-60 °C

A flask was charged with a solution of oxalyl chloride (3.2 ml, 33 mmol) in dichloromethane (60 ml). The solution was cooled to −60° C., and a solution of dimethylsulfoxide (5.1 ml, 66 mmol) in dichloromethane (10 ml) was added dropwise, such that the internal temperature was maintained at −60° C. This was followed by the dropwise addition of a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (5.6 g, 30 mmol) in dichloromethane (25 ml). The resulting solution was allowed to stir for 1 hour −60° C., then triethyamine (21 ml) was added and the mixture was allowed to warm to room temperature. The solution was diluted with 150 ml of water and extracted with dichloromethane (2×150 ml). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to afford tert-butyl 3-oxopyrrolidine-1-carboxylate as a white solid.

1. temperaturewas maintained at −60° C
2. temperatureto warm to room temperature
3. extractionextracted with dichloromethane (2×150 ml)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-3c630e0f90a143d0b10306bfa36befeb

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455477B2