Dimethyl Sulfoxide → tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate

Temperature

-78 °C

DMSO (1.4 mL, 19.69 mmol) in dichloromethane (2 mL) was added dropwise to a solution of oxalyl chloride (0.86 mL, 9.85 mmol) in dichloromethane (10 mL) at −78° C. After 10 min at −78° C., (R)-tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (1.8 g, 8.95 mmol) in dichloromethane (6 mL) was added dropwise. After the resulting mixture was stirred at −78° C. for 30 min, triethylamine (6.2 mL, 44.75 mmol) was added and the mixture was stirred at −78° C. for 45 min then at room temperature for 30 min. Water was added to the reaction mixture and the two layers were separated. The organic layer was washed with water, dried over sodium sulfate, filtered and the solvent removed. The crude material was purified by flash chromatography on silica gel eluting with 0 to 50% ethyl acetate/hexanes to afford 0.6 g of (R)-tert-butyl 3-formylpyrrolidine-1-carboxylate as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ 9.60 (s, 1H), 3.54 (dd, 1H), 3.32-3.21 (m, 2H), 3.12 (m, 2H), 2.04 (m, 2H), 1.39 (s, 9H).

1. stirringthe mixture was stirred at −78° C. for 45 min
2. waitat room temperature for 30 min
3. customthe two layers were separated
4. washThe organic layer was washed with water
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customthe solvent removed
8. customThe crude material was purified by flash chromatography on silica gel eluting with 0 to 50% ethyl acetate/hexanes

ORD record

ord-2c56f3974d90419690fb5d8b1464aa5c

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193714B2