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

Temperature

-60 °C

Dimethylsulfoxide (DMSO; 1.56 ml; 22 mmol) was added over 15 minutes to a solution of oxalyl chloride (0.97 ml; 11 mmol) in CH2Cl2 (20 ml) at -60° C. After stirring 15 minutes at -60° C., the title compound of Step (A) (1.87 g; 10 mmol) was added dropwise over 15 minutes as a solution in CH2Cl2 (20 ml). After stirring 15 minutes at -60° C., diisopropylethylamine (8.75 ml; 50 mmol) was added over 5 minutes. After stirring 15 minutes at -60° C., the reaction mixture was allowed to warm to room temperature and stir 30 minutes. The reaction mixture was diluted with CH2Cl2 (100 ml) and was washed with saturated KHSO4 solution (2×100 ml), saturated NaHCO3 solution (100 ml) and brine (100 ml). Drying (MgSO4) and concentration afforded 1.87 g (99%) of the title compound of this step as a light yellow oil.

1. stirringAfter stirring 15 minutes at -60° C.
2. stirringAfter stirring 15 minutes at -60° C.
3. temperatureto warm to room temperature
4. stirringstir 30 minutes
5. washwas washed with saturated KHSO4 solution (2×100 ml), saturated NaHCO3 solution (100 ml) and brine (100 ml)
6. customDrying
7. concentration(MgSO4) and concentration

ORD record

ord-ed25e6f8f01f49949ca5443b7d564847

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05846990