Hydrochloric Acid → (2R,4S)-1-Benzyl-4-methyl-5-oxo-pyrrolidine-2-carboxylic Acid

To a solution of (R)-1-benzyl-5-oxopyrrolidine-2-carboxylic acid (1000 mg, 4.56 mmol) in 55 ml of THF 10.03 ml of a 1M lithium bis(trimethylsilyl)amide solution in THF (10.03 mmol) were added slowly at −10° C., and stirring was continued at this temperature for 1 h. Subsequently iodomethane (0.284 ml, 647 mg, 4.56 mmol) in 9 ml of THF were added (slight exothermic reaction), and the reaction was completed by stirring overnight at room temperature. The brown reaction mixture was acidified using 2M HCl, extracted three times with ethyl acetate. The combined organic layers were then washed with brine, dried over Na2SO4 and the solvent evaporated under reduced pressure. The title compound was obtained as a brown oil, which was reacted in the next step without further purification (890 mg of raw material, yield: 84%).

1. custom(slight exothermic reaction)
2. stirringby stirring overnight at room temperature
3. extractionextracted three times with ethyl acetate
4. washThe combined organic layers were then washed with brine
5. dry with materialdried over Na2SO4
6. customthe solvent evaporated under reduced pressure

ORD record

ord-30ef3ed38e1a496f9d35d4df19276c4e

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018206B2