tert-butyl(2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoate → tert-Butyl(2S)-2-[(3S)-3-amino-2-oxopyrrolidin-1-yl)propanoate

HRID 33421Notes

Reaction equation

HRID 33421 reaction equation
C(OC([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@@H:17]([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]1=[O:26])=O)C1C=CC=CC=1>[Pd].C(O)C>[NH2:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@@H:17]([CH3:25])[C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C:13]1=[O:26]

Participants

4

Reactant 1

HCID 16124826tert-butyl(2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoate

Product 1

HCID 69222344tert-Butyl(2S)-2-[(3S)-3-amino-2-oxopyrrolidin-1-yl)propanoateYield 101.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl(2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (2.82 g), 10% palladium on carbon (0.3 g) and ethanol (150 ml) was stirred under an atmosphere of hydrogen for 18 h. The reaction mixture was filtered through Harbolite™ and the filtrate was concentrated under reduced pressure to give the title compound (1.8 g) as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-d83c8463fdc94a0cb558e133bd72957f
Source dataset
uspto-grants-2008_09
Patent number
US07429587B2

Reaction notes

Loading…