N2 (benzyloxycarbonyl)-N1-tert.butyl-4(R)-hydroxy-L-prolinamide → N1-tert.butyl-4(R)-hydroxy-L-prolinamide

HRID 466883Notes

Reaction equation

HRID 466883 reaction equation
N#N.C(OC([C@@:13]1([C:23]([NH2:25])=[O:24])[CH2:17][C@@H:16]([OH:18])[CH2:15][N:14]1[C:19]([CH3:22])([CH3:21])[CH3:20])=O)C1C=CC=CC=1>C(O)C.[Pd]>[C:19]([N:14]1[CH2:15][C@H:16]([OH:18])[CH2:17][C@H:13]1[C:23]([NH2:25])=[O:24])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 1

HCID 86746270N2 (benzyloxycarbonyl)-N1-tert.butyl-4(R)-hydroxy-L-prolinamide

Product 1

HCID 57132046N1-tert.butyl-4(R)-hydroxy-L-prolinamideYield 108.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.224 g of N2 -(benzyloxycarbonyl)-N1 -tert.butyl-4(R)-hydroxy-L-prolinamide was dissolved in 20 ml of ethanol and hydrogenated over 50 mg of 10% palladium-on-carbon at room temperature and under atmospheric pressure for 2 hours. The catalyst was filtered off and the filtrate was evaporated to give 0.13 g of N1 -tert.butyl-4(R)-hydroxy-L-prolinamide which was used in the next step without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2c15159b070d4529b06f9670840fafe6
Source dataset
uspto-grants-1992_10
Patent number
US05157041

Reaction notes

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