(3R)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid → tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

To a stirred solution of (R)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (1.21 g, 5.6 mmol) in THF (30 mL) at 0° C. was added borane THF (1.0 M, 17 mL, 16.9 mmol) dropwise. The resulting mixture was warmed to rt over 30 min and then heated at 45° C. for 1 h, then at 55° C. for 90 min. The reaction mixture was then cooled to 0° C. and quenched carefully with 3N HCl (30 mL). The resulting mixture was stirred at rt for 20 min before it was extracted with Et2O (50 mL). The organic layer was washed with sat. NaHCO3 (20 mL) brine (20 mL), dried over NaSO4, filtered, and concentrated under reduced pressure to give (R)-tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (1.1 g, 91%) as a colorless oil.

1. temperatureheated at 45° C. for 1 h
2. temperatureThe reaction mixture was then cooled to 0° C.
3. customquenched carefully with 3N HCl (30 mL)
4. extractionwas extracted with Et2O (50 mL)
5. washThe organic layer was washed with sat. NaHCO3 (20 mL) brine (20 mL)
6. dry with materialdried over NaSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-270c2dda25664608a40cb8baa2cf4f10

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296722B2