t-Butyl beta-[4-(benzyloxycarbonylamino)cyclohexyl]acrylate → HCID 18919405, compound

HRID 1290990Notes

Reaction equation

HRID 1290990 reaction equation
C(OC([NH:11][CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[CH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14][CH2:13]1)=O)C1C=CC=CC=1>CO.[C].[Pd]>[NH2:11][CH:12]1[CH2:13][CH2:14][CH:15]([CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 54405513t-Butyl beta-[4-(benzyloxycarbonylamino)cyclohexyl]acrylate

Product 1

HCID 18919405HCID 18919405, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

t-Butyl β-[4-(benzyloxycarbonylamino)cyclohexyl]acrylate (7.00 g, 19.5 mmol) was dissolved in methanol (200 ml) and 10% palladium-carbon (700 mg) was added. The mixture was stirred at room temperature for 24 hours under a hydrogen atmosphere. The reaction mixture was filtrated and low boiling matters were distilled away from the filtrate under reduced pressure. The residue was washed with a mixed solution of n-hexane and ethyl acetate to give 3.78 g of t-butyl 3-(4-aminocyclohexyl)propionate as a colorless solid (85%).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. distillationlow boiling matters were distilled away from the filtrate under reduced pressure
  3. washThe residue was washed with a mixed solution of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-d9a5140d12ab471b8d6e1131f708b0f3
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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