4-Hydroxyimino-6-phenyl-hexanoic acid → (RS)-4-Amino-6-phenyl-hexanoic acid

HRID 852893Notes

Reaction equation

HRID 852893 reaction equation
O[N:2]=[C:3]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4][CH2:5][C:6]([OH:8])=[O:7]>C(O)C.[Pd]>[NH2:2][CH:3]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 600707174-Hydroxyimino-6-phenyl-hexanoic acid

Product 1

HCID 11171785(RS)-4-Amino-6-phenyl-hexanoic acidYield 5.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the oximes 100 (2.7 g 12.2 mmol) in ethanol (40 mL) was hydrogenated over 10% Pd—C at 40 psi and 50° C. for 3 days. The catalyst was filtered off and the solvent was evaporated. The residue was partitioned between ether and 0.1 M HCl and the aqueous layer was lyophilized giving 101 as a white powder (130 mg, 5%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between ether and 0.1 M HCl

Sources & evidence

ORD record
ord-e3c36714823841a9915ddfb1e80298cf
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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