Dichloromethane → 1-[(3S)-3-hydroxypyrrolidin-1-yl]propan-1-one

Temperature

-10 °C

(S)-Pyrrolidin-3-ol (10.0 g, 81.0 mmol), triethylamine (23.6 mL, 170.0 mmol) and CH2Cl2 (150 mL) were combined in a pear-shaped flask to give a beige suspension. The mixture was cooled to −10° C. and propionyl chloride (7.06 mL, 81.0 mmol) was added dropwise over 15 min, maintaining the temperature between −10 to 0° C. The resulting beige suspension was stirred for 2 h at 0° C. MeOH (9.8 mL) was added and the mixture allowed to warm to room temperature then stirred for 1 h to give a brown solution. The mixture was evaporated in vacuo to give a beige residue which was stirred in diethylether (200 mL) and filtered. The filtrate was evaporated in vacuo to give 1-((S)-3-hydroxy-pyrrolidin-1-yl)-propan-1-one as a yellow oil (11.23 g, 95% yield). 1H-NMR (400 MHz, DMSO-d6, 298 K): δ ppm 0.92-1.02 m, 3H) 1.67-1.97 (m, 2H) 2.13-2.28 (m, 2H) 3.18-3.52 (m, 4H) 4.17-4.32 (m, 1H) 4.85-4.97 (m, 1H). LCMS: [M+H]+=144.0

1. customto give a beige suspension
2. temperaturemaintaining the temperature between −10 to 0° C
3. temperatureto warm to room temperature
4. stirringthen stirred for 1 h
5. customto give a brown solution
6. customThe mixture was evaporated in vacuo
7. customto give a beige residue which
8. filtrationfiltered
9. customThe filtrate was evaporated in vacuo

ORD record

ord-8e40cff91f2c4569a91fca9a1ca6adca

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653092B2