HCID 68713392, compound → HCID 68717082, compound

HRID 1911530Notes

Reaction equation

HRID 1911530 reaction equation
[NH2:1][C@@H:2](/[CH:5]=[C:6](/[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)\[CH2:7][CH3:8])[CH2:3][OH:4]>C(O)C.[Pt]>[NH2:1][C@@H:2]([CH2:5][CH:6]([C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[CH2:7][CH3:8])[CH2:3][OH:4]

Participants

4

Reactant 1

HCID 68713392HCID 68713392, compound

Product 1

HCID 68717082HCID 68717082, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of (E)-(S)-2-amino-4-(4-chloro-phenyl)-hex-3-en-1-ol (0.52 g) at r.t. in ethanol (30 ml) under an argon atmosphere was added 5% Pt/C (180 mg). The mixture was stirred at r.t. under a hydrogen atmosphere for 16 hrs. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (S)-2-amino-4-(4-chloro-phenyl)-hexan-1-ol (mainly one epimer) (0.157 g, 30%) as colourless oil. MS (ISP): 230.3 ([{37Cl}M+H]+), 228.2 ([{35Cl}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: heptane/EtOAc)

Sources & evidence

ORD record
ord-ed06cf9921da499eb8111213c5808ba8
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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