Ethyl 4-(dibenzylamino)-2-ethylcyclopentanecarboxylate → Ethyl 4-amino-2-ethylcyclopentanecarboxylate

HRID 1969617Notes

Reaction equation

HRID 1969617 reaction equation
C([N:8](CC1C=CC=CC=1)[CH:9]1[CH2:13][CH:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]([CH2:19][CH3:20])[CH2:10]1)C1C=CC=CC=1.[H][H]>CCO.[OH-].[OH-].[Pd+2]>[NH2:8][CH:9]1[CH2:13][CH:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]([CH2:19][CH3:20])[CH2:10]1

Participants

5

Reactant 2

HCID 58009964Ethyl 4-(dibenzylamino)-2-ethylcyclopentanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58009905Ethyl 4-amino-2-ethylcyclopentanecarboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a vessel containing a slurry of 20 wt % Pd(OH)2 on C (12.9 g, 18.4 mmol) in EtOH (1.0 L) was added ethyl 4-(dibenzylamino)-2-ethylcyclopentanecarboxylate (129 g, 352 mmol, Preparation #X.1). The reaction was shaken for about 90 min at about 50° C. under about 30 psi of hydrogen. After removal of the hydrogen source and introduction of a nitrogen atmosphere, the resulting mixture was filtered through a pad of Celite® and the filtrate was concd under reduced pressure to give ethyl 4-amino-2-ethylcyclopentanecarboxylate (64.5 g, 99%) as a yellow syrup: 1H NMR (CDCl3) δ 4.03-3.88 (m, 2H), 3.17 (m, 1H), 2.68 (m, 1H), 2.09-2.02 (m, 2H), 2.02-1.94 (m, 2H), 1.84 (m, 1H), 1.58-1.48 (m, 1H), 1.32-1.18 (m, 1H), 1.09 (m, 3H), 1.03 (m, 2H), 0.78-0.69 (m, 3H).

Workup

  1. customAfter removal of the hydrogen source and introduction of a nitrogen atmosphere
  2. filtrationthe resulting mixture was filtered through a pad of Celite®

Sources & evidence

ORD record
ord-8b3559f05fbc4d4ebd53b852b7c919c7
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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