Phenylmethyl 4-(dimethylamino)-3,3-dimethyl-1-pyrrolidinecarboxylate → HCID 55299466, compound

HRID 1366504Notes

Reaction equation

HRID 1366504 reaction equation
[CH3:1][N:2]([CH3:20])[CH:3]1[CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[CH2:5][C:4]1([CH3:19])[CH3:18]>CO.[Pd]>[CH3:1][N:2]([CH3:20])[CH:3]1[C:4]([CH3:19])([CH3:18])[CH2:5][NH:6][CH2:7]1

Participants

4

Reactant 1

HCID 66936116Phenylmethyl 4-(dimethylamino)-3,3-dimethyl-1-pyrrolidinecarboxylate

Product 1

HCID 55299466HCID 55299466, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of racemic phenylmethyl 4-(dimethylamino)-3,3-dimethyl-1-pyrrolidinecarboxylate (assumed 0.6565 g, 2.376 mmol) in MeOH was added 10% Pd/C (50% water, 195 mg). The mixture was hydrogenated under balloon pressure for 1 h, and then filtered. The solution was concentrated in vacuo to afford racemic N,N,4,4-tetramethyl-3-pyrrolidinamine (0.3479 g, quantitative yield) as an almost colorless oil. LCMS: (M+H)+: 143.1.

Workup

  1. filtrationfiltered
  2. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-4fc16c1d246949418aee1b5b62378774
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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