Acetic Acid → (1R)-1-(3-chlorophenyl)-2-(4-phenylcyclohexylamino) ethanol

HRID 1108774Notes

Reaction equation

HRID 1108774 reaction equation
C(O)(=O)C.[NH2:5][CH2:6][C@@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)[OH:8].[C:16]1([CH:22]2[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H][H]>CO.O=[Pt]=O>[Cl:15][C:11]1[CH:10]=[C:9]([C@@H:7]([OH:8])[CH2:6][NH:5][CH:25]2[CH2:24][CH2:23][CH:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:27][CH2:26]2)[CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 786054-PhenylcyclohexanoneHCID 9920489(R)-2-Amino-1-(3-chlorophenyl)ethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 54333897(1R)-1-(3-chlorophenyl)-2-(4-phenylcyclohexylamino) ethanolYield 4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Acetic acid (1 ml) and PtO2 (160 mg) were added to a solution of (R)-2-amino-1-(3-chlorophenyl) ethanol (600 mg) and 4-phenylcyclohexanone (610 mg) in methanol (30 ml), and hydrogen addition was carried out at room temperature. After consumption of the starting materials, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. Separation and purification by silica gel column chromatography (chloroform:methanol=30:1) gave 43 mg of (1R)-1-(3-chlorophenyl)-2-(4-phenylcyclohexylamino) ethanol (4.0% yield).

Workup

  1. customwas carried out at room temperature
  2. customAfter consumption of the starting materials
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customSeparation and purification by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-cdb50a1fc331486aa07540a408ab6f05
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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