(S)-Benzyl 2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate → (2S)-N,N-dimethylpyrrolidine-2-carboxamide

HRID 1285002Notes

Reaction equation

HRID 1285002 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=O)C1C=CC=CC=1.[H][H]>C(O)C.[C].[Pd]>[CH3:19][N:18]([CH3:20])[C:16]([C@@H:12]1[CH2:13][CH2:14][CH2:15][NH:11]1)=[O:17]

Participants

5

Reactant 2

HCID 13564352(S)-Benzyl 2-(dimethylcarbamoyl)pyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 7408249(2S)-N,N-dimethylpyrrolidine-2-carboxamideYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 86 ml of ethanol was dissolved 4.3 g of compound (88) and after adding thereto 210 mg of 10% palladium-carbon, the mixture was stirred vigorously for 90 minutes in a hydrogen stream, After filtering off the catalyst, ethanol was distilled off under reduced pressure to provide 2.19 g of crude (S)-N,N-dimethyl-2-pyrrolidinecarboxamide (89).

Workup

  1. additionafter adding
  2. filtrationAfter filtering off the catalyst, ethanol
  3. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-9f85be37924f41cbbf5059ae1c55f018
Source dataset
uspto-grants-1986_01
Patent number
US04564609

Reaction notes

Loading…