benzyl(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-ylcarbamate → (3S)-3-Amino-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]pyrrolidin-2-one

HRID 7291Notes

Reaction equation

HRID 7291 reaction equation
[CH3:1][C@H:2]([N:11]1[CH2:15][CH2:14][C@H:13]([NH:16]C(=O)OCC2C=CC=CC=2)[C:12]1=[O:27])[C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4]>[Pd].C(O)C>[NH2:16][C@H:13]1[CH2:14][CH2:15][N:11]([C@@H:2]([CH3:1])[C:3]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)=[O:4])[C:12]1=[O:27]

Participants

4

Reactant 1

HCID 16125563benzyl(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-ylcarbamate

Product 1

HCID 16125562(3S)-3-Amino-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]pyrrolidin-2-oneYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl (3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-ylcarbamate (20 g), 10% palladium on carbon (2 g) and ethanol (1.3 l) was stirred under an atmosphere of hydrogen for 16 h. The reaction mixture was filtered through Celite™ and the filtrate was concentrated under reduced pressure to give the title compound (12.3 g) as a pale white oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c54c7d41fb7c4d1fb6d25147d00d8589
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Reaction notes

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