HCID 53641990, compound → HCID 54009054, compound

HRID 399528Notes

Reaction equation

HRID 399528 reaction equation
[C:1]([O:5][C:6](=[O:22])[C@@H:7]1[CH2:11][C@@H:10]([N:12]=[N+]=[N-])[CH2:9][N:8]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:22])[C@@H:7]1[CH2:11][C@@H:10]([NH2:12])[CH2:9][N:8]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 53641990HCID 53641990, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54009054HCID 54009054, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution (4R)-1-(tert-butyloxycarbonyl)-4-azido-L-proline tert-butyl ester (191 mg, 0.611 mmol) in 90% ethanol (15 mL) was hydrogenated in the presence of 10% palladium-on-charcoal (40 mg) under a balloon atmosphere of hydrogen gas for one hour. The catalyst was removed by filtration through Celite, the filter washed with methanol, and the combined filtrate and washings evaporated. The title compound was obtained as a colorless oil after drying under high vacuum; yield 177 mg.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washthe filter washed with methanol
  3. customthe combined filtrate and washings evaporated

Sources & evidence

ORD record
ord-d47d0d7f6b084d189a052f671a8f1bb2
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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