HCID 14555447, compound → tert-Butyl {(S)-1-methyl-2-oxo-2-[(S)-pyrrolidin-3-ylamino]ethyl}carbamate

HRID 232038Notes

Reaction equation

HRID 232038 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:25])[NH:7][CH:8]([CH3:24])[C:9](=[O:23])[NH:10][CH:11]1[CH2:15][CH2:14][N:13](CC2C=CC=CC=2)[CH2:12]1)([CH3:4])[CH3:3].[H][H]>CO.[Pd]>[CH3:4][C:2]([O:5][C:6](=[O:25])[NH:7][CH:8]([CH3:24])[C:9](=[O:23])[NH:10][CH:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 14555447HCID 14555447, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14555449tert-Butyl {(S)-1-methyl-2-oxo-2-[(S)-pyrrolidin-3-ylamino]ethyl}carbamateYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6.9 g (20 mmol) of [1-methyl-2-oxo-2-[(1-(phenylmethyl)-3-pyrrolidinyl)amino]ethyl]-carbamic acid 1,1-dimethylethyl ester in 100 ml of methanol was treated with 1.0 g of 20% palladium on carbon and shaken in a hydrogen atmosphere at pressures of 33.6 to 52.7 psi and temperatures of 23.5°-27.0 for 18 hours. The catalyst was removed by filtration and the solvent evaporated to give 5.0 g of the title compound as a viscous liquid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-5aee477c029c4d0785e5824cda5d9c86
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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