HCID 68716058, compound → HCID 68716614, compound

HRID 1911535Notes

Reaction equation

HRID 1911535 reaction equation
[NH2:1][C@@H:2](/[CH:5]=[C:6](/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)\[CH2:7][CH3:8])[CH2:3][OH:4]>CO.[Pd]>[NH2:1][C@@H:2]([CH2:5][CH:6]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:7][CH3:8])[CH2:3][OH:4]

Participants

4

Reactant 1

HCID 68716058HCID 68716058, compound

Product 1

HCID 68716614HCID 68716614, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (E)-(S)-2-amino-4-phenyl-hex-3-en-1-ol (1.0 g) at r.t. in methanol (50 ml) under an argon atmosphere was added 10% Pd/C (278 mg). The mixture was stirred at r.t. under a hydrogen atmosphere for 30 min. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: dichloromethane/methanol) to give (S)-2-amino-4-phenyl-hexan-1-ol (mainly one epimer) (0.81 g, 80%) as a colourless oil. MS (ISP): 194.4 ([M+H ]+).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography (SiO2; gradient: dichloromethane/methanol)

Sources & evidence

ORD record
ord-a9837408ff484958a4772a01dba03b6a
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

Loading…