Dimethyl Sulfoxide → tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Temperature

-75 °C

A mixture of oxalyl chloride (14.1 mL, 161 mmol) in CH2Cl2 (331 mL) was cooled to −75° C. Dimethylsulfoxide (19.4 mL, 273 mmol) in CH2Cl2 (70 mL) was slowly added over 30 minutes followed by stirring at −75° C. for an additional 15 minutes. At −75° C. (S)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (25.0 g, 124 mmol) in CH2Cl2 (132 mL) was added slowly over one hour, followed by a further 15 minutes of stirring. Then, still at −75° C., Et3N (87 mL, 621 mmol) was added over 30 minutes followed by another 15 minutes of stirring. Mixture was then allowed to stir at 0° C. for 90 minutes. Mixture was quenched with 10% aqueous Citric acid at 0° C. The mixture was diluted with 10% aqueous Citric acid and partitioned. Organic was washed with H2O (5×150 mL) and Brine. The organic was then dried (MgSO4), filtered and concentrated to afford 24.7 g (100%) of the title compound. MS (ESI) m/z 200 (M+H)+.

1. waitfollowed by a further 15 minutes
2. stirringof stirring
3. waitfollowed by another 15 minutes
4. stirringof stirring
5. stirringto stir at 0° C. for 90 minutes
6. customMixture was quenched with 10% aqueous Citric acid at 0° C
7. additionThe mixture was diluted with 10% aqueous Citric acid
8. custompartitioned
9. washOrganic was washed with H2O (5×150 mL) and Brine
10. dry with materialThe organic was then dried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-bdb27139f30c41859e35f46a959b0e98

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691938B2