(E)-(2S)-2-Amino-5-phenyl-hex-4-en-1-ol → (2S)-2-Amino-5-phenyl-hexan-1-ol

HRID 1026115Notes

Reaction equation

HRID 1026115 reaction equation
[NH2:1][C@@H:2]([CH2:5]/[CH:6]=[C:7](/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)\[CH3:8])[CH2:3][OH:4]>CO.[Pd]>[NH2:1][C@@H:2]([CH2:5][CH2:6][CH:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:8])[CH2:3][OH:4]

Participants

4

Reactant 1

HCID 67177671(E)-(2S)-2-Amino-5-phenyl-hex-4-en-1-ol

Product 1

HCID 67177481(2S)-2-Amino-5-phenyl-hexan-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-(2S)-2-amino-5-phenyl-hex-4-en-1-ol (180 mg) in methanol (25 ml) at room temperature was added 10% palladium on charcoal (50 mg). The mixture was stirred under an atmosphere of hydrogen (1 atm) at room temperature for 2 h. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to yield a colourless oil, (160 mg, 88%); MS (ISP): 194.3 ([M+H]+).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto yield a colourless oil, (160 mg, 88%)

Sources & evidence

ORD record
ord-bab8e08305fb4bcc83219559e0908df0
Source dataset
uspto-grants-2014_05
Patent number
US08729113B2

Reaction notes

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