(S)-2-amino-3-methyl-4-phenyl-but-3-en-1-ol → (S)-2-amino-3-methyl-4-phenyl-butan-1-ol

HRID 1911525Notes

Reaction equation

HRID 1911525 reaction equation
[NH2:1][C@@H:2]([C:5]([CH3:13])=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][OH:4]>CCO.[Pd]>[NH2:1][C@@H:2]([CH:5]([CH3:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][OH:4]

Participants

4

Reactant 1

HCID 68717428(S)-2-amino-3-methyl-4-phenyl-but-3-en-1-ol

Product 1

HCID 68716469(S)-2-amino-3-methyl-4-phenyl-butan-1-olYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (S)-2-amino-3-methyl-4-phenyl-but-3-en-1-ol (115 mg) in EtOH (5 ml) was hydrogenated at normal pressure (balloon) overnight in the presence of 10% Pd/C (10 mg). The reaction mixture was filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give (S)-2-amino-3-methyl-4-phenyl-butan-1-ol (57 mg, 49%) as light yellow oil. MS (ISP): 180.3 ([M+H]+))

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-76fe52cc44aa4d7087dd3688eb8b7f7d
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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