(S)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-hexanoic acid ethyl ester → Ethyl (3S)-3-aminohexanoate

HRID 388489Notes

Reaction equation

HRID 388489 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@@H:6]([N:10](CC1C=CC=CC=1)[C@H](C1C=CC=CC=1)C)[CH2:7][CH2:8][CH3:9])[CH3:2]>CCO.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@@H:6]([NH2:10])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

4

Reactant 1

HCID 59497521(S)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-hexanoic acid ethyl ester

Product 1

HCID 10773249Ethyl (3S)-3-aminohexanoateYield 87.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-hexanoic acid ethyl ester (20.8 g, 59 mmol) in EtOH (50 mL) is added Pd(OH)2 (20% in carbon) (2 g). The mixture is stirred under hydrogen atmosphere with 40 psi for 16 hours. The mixture is filtered and the filtrate is concentrated to give the title compound (8.2 g, 87%).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-3de742923b3543eea7367d494c853c4f
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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