HCID 18340730, compound → Methyl 3-[(1,1-dimethylethoxy)carbonyl]-5-oxo-3-pyrrolidineacetate

HRID 1485092Notes

Reaction equation

HRID 1485092 reaction equation
[C:1]([C:3]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH2:9][C:10](OC)=[O:11])[CH2:4][C:5]([O:7][CH3:8])=[O:6])#[N:2].[H][H]>CO.[Ni]>[CH3:8][O:7][C:5](=[O:6])[CH2:4][C:3]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][C:10](=[O:11])[NH:2][CH2:1]1

Participants

5

Reactant 2

HCID 18340730HCID 18340730, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18340822Methyl 3-[(1,1-dimethylethoxy)carbonyl]-5-oxo-3-pyrrolidineacetateYield 38.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution in methanol (70 mL) of the compound (5.00 g) obtained in step (1) above, a Raney nickel catalyst (about 7.5 g) was added. The mixture was stirred at 70° C. for 8 hours in a hydrogen atmosphere with 0.4 megapascals (MPa). After being cooled to room temperature, the reaction mixture was filtered through Celite (registered trademark) and the filtrate was concentrated under reduced pressure. To the resulting residue, diethyl ether (50 mL) and hexane (10 mL) were added and the mixture was stirred at room temperature for 15 minutes. The resulting precipitate was recovered by filtration to give tert-butyl 3-(2-methoxy-2-oxoethyl)-5-oxopyrrolidine-3-carboxylate as a colorless solid (1.75 g).

Workup

  1. filtrationthe reaction mixture was filtered through Celite (registered trademark)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the resulting residue, diethyl ether (50 mL) and hexane (10 mL) were added
  4. filtrationThe resulting precipitate was recovered by filtration

Sources & evidence

ORD record
ord-5c89d577111e4686bf53df92af974c38
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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