Methanol → 3-Amino-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide

HRID 491911Notes

Reaction equation

HRID 491911 reaction equation
C([N:8](C(C1C=CC=CC=1)C)[CH:9]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:10][C:11]([NH:13][CH2:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:12])C1C=CC=CC=1.CO.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:8][CH:9]([CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)[CH2:10][C:11]([NH:13][CH2:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:12]

Participants

7

Reactant 3

HCID 887MethanolHCID 670237123-[Benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamideHCID 178418361HCID 178418361, compound

Product 1

HCID 670237583-Amino-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a Parr bottle 10% Pd/C (0.8 g) was cooled to −78° C., followed by addition of a solution of 3-[benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide (0.8 g, 1.78 mmol) in ethyl acetate (10 mL), ethanol (100 mL), and methanol (20 mL). The resulting mixture was subjected to hydrogen atmosphere and shaken for 3 h. The hydrogen was purged with nitrogen, the reaction mixture was filtered (glass fiber filter paper) and the solvent was evaporated under reduced pressure to yield a residue.

Workup

  1. customThe hydrogen was purged with nitrogen
  2. filtrationthe reaction mixture was filtered
  3. filtration(glass fiber filter paper)
  4. customthe solvent was evaporated under reduced pressure
  5. customto yield a residue

Sources & evidence

ORD record
ord-e0a7adef03514bba81d8abdcb9d16fbf
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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