4-Hydroxyimino-6-phenyl-hexanoic acid → (RS)-4-Amino-6-phenyl-hexanoic acid
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
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe catalyst was filtered off
- customthe solvent was evaporated
- 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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