[1-Methyl-2-[[(3-methyl-1-(phenylmethyl)-3-pyrrolidinyl)methyl]amino]-2-oxoethyl]carbamic acid, 1,1-dimethylethyl ester → [1-Methyl-2-[[(3-methyl-3-pyrrolidinyl)methyl]amino]-2-oxoethyl]carbamic acid, 1,1-dimethylethyl ester

HRID 232055Notes

Reaction equation

HRID 232055 reaction equation
[CH3:1][CH:2]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:3]([NH:5][CH2:6][C:7]1([CH3:19])[CH2:11][CH2:10][N:9](CC2C=CC=CC=2)[CH2:8]1)=[O:4].[H][H]>CO.[Pd]>[CH3:1][CH:2]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:3]([NH:5][CH2:6][C:7]1([CH3:19])[CH2:11][CH2:10][NH:9][CH2:8]1)=[O:4]

Participants

5

Reactant 2

HCID 14555506[1-Methyl-2-[[(3-methyl-1-(phenylmethyl)-3-pyrrolidinyl)methyl]amino]-2-oxoethyl]carbamic acid, 1,1-dimethylethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 14555508[1-Methyl-2-[[(3-methyl-3-pyrrolidinyl)methyl]amino]-2-oxoethyl]carbamic acid, 1,1-dimethylethyl esterYield 96.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 23.1 g (61.6 mmol) of [1-methyl-2-[[(3-methyl-1-(phenylmethyl)-3-pyrrolidinyl)methyl]-amino]-2-oxoethyl]carbamic acid, 1,1-dimethylethyl ester in 400 ml of methanol was treated with 3.0 g of 20% palladium on carbon and shaken in a hydrogen atmosphere at temperatures of 22°-26° and pressures of 48.7-53.4 psi for 2.5 hours. The catalyst was removed by filtering through celite and the filtrate was evaporated in vacuo to give 17.0 g of the title compound.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through celite
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-e58a1ba47d80457ebf084c8ccda6ed13
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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