HCID 21260503, compound → HCID 21260560, compound

HRID 634765Notes

Reaction equation

HRID 634765 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:10]=2)=[CH:5][CH:4]=1>[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 21260503HCID 21260503, compound

Product 1

HCID 21260560HCID 21260560, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (RS)-[3-(4-methoxy-phenyl)-cyclohex-2-enyl]-(4-phenyl-butyl)-amine (2.4 g, 7.15 mmol), 10% Pd/C (0.48 g) and MeOH (50 ml) was hydrogenated for 3 h. Removal of the catalyst, evaporation of the solvent and separation of the isomers by flash-chromatography over SiO2 (Biotage 40, 90 g) eluting with AcOEt gave (1RS,3SR)-[3-(4-methoxy-phenyl)-cyclohexyl]-(4-phenyl-butyl)-amine (1.2 g, 50%, light yellow oil, MS: m/e=338.3 (M+H+)) and (1RS,3RS)-[3-(4-methoxy-phenyl)-cyclohexl]-4-phenyl-butyl)-amine (0.43 g, 18%, light yellow oil, MS: m/e=338.3 (M+H+)).

Workup

  1. customRemoval of the catalyst, evaporation of the solvent and separation of the isomers by flash-chromatography over SiO2 (Biotage 40, 90 g)
  2. washeluting with AcOEt

Sources & evidence

ORD record
ord-b51220d97c8849fe947135a1986e9a87
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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