Benzyl 2,2-dimethyl-3-oxocyclopentylcarbamate → 3-Amino-2,2-dimethylcyclopentanone

HRID 1408934Notes

Reaction equation

HRID 1408934 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6](=[O:7])[CH2:5][CH2:4][CH:3]1[NH:8]C(=O)OCC1C=CC=CC=1>[Pd].CO>[NH2:8][CH:3]1[CH2:4][CH2:5][C:6](=[O:7])[C:2]1([CH3:19])[CH3:1]

Participants

4

Reactant 1

HCID 68291986Benzyl 2,2-dimethyl-3-oxocyclopentylcarbamate

Product 1

HCID 682916003-Amino-2,2-dimethylcyclopentanoneYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 2,2-dimethyl-3-oxocyclopentylcarbamate (950 mg, 3.64 mmol, from Step 1) and 10% palladium on carbon (193 mg) in methanol (20 mL) was stirred under hydrogen (20 psi) for 2 h. After filtration to remove the catalyst, the filtrate was concentrated to give crude 3-amino-2,2-dimethylcyclopentanone (430 mg), which was used in the next reaction without purification.

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b6e8d076ceb749889952ee9e61566403
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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