Reaction #82335

ord-c84d36a48b5a40ceae6a492f0cd29e24

Reaction equation

CC(C)CCN1CCC[C@]1(C(N)=O)C(=O)OCc1ccccc1.N#N
N2 (benzyloxycarbonyl)-N1 -isopentyl-L-prolinamide
→
CC(C)CCN1CCC[C@H]1C(N)=O
N1 -isopentyl-L-prolinamide
Yield 111.5%

Reactants

CC(C)CCN1CCC[C@]1(C(N)=O)C(=O)OCc1ccccc1.N#N
N2 (benzyloxycarbonyl)-N1 -isopentyl-L-prolinamide

Reagents

[Pd]
palladium-on-carbon

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe catalyst was removed by filtration
  2. 2
    Otherthe filtrate was evaporated

Procedure

A solution of 5.73 g of N2 -(benzyloxycarbonyl)-N1 -isopentyl-L-prolinamide in 600 ml of ethanol was hydrogenated over 0.8 g of 10% palladium-on-carbon catalyst for 3.75 hours. The catalyst was removed by filtration and the filtrate was evaporated to give 3.4 g of N1 -isopentyl-L-prolinamide as an oil which was used without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05620987uspto-grants-1997_04