HCID 90876343, compound → isobutyric acid (1R*,2R*,4R*)-(5RS)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-2-yl ester

HRID 220321Notes

Reaction equation

HRID 220321 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][CH2:12][N:13]([CH3:36])[CH2:14][CH2:15][C@:16]1([O:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH2:21][C@H:20]2[CH2:22][CH2:23][C@@H:17]1[CH:18]=[C:19]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CCO.[Pd]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][CH2:12][N:13]([CH3:36])[CH2:14][CH2:15][C@:16]1([O:30][C:31](=[O:35])[CH:32]([CH3:33])[CH3:34])[CH2:21][C@H:20]2[CH2:22][CH2:23][C@@H:17]1[CH2:18][CH:19]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 1

HCID 90876343HCID 90876343, compound

Product 1

HCID 91135258isobutyric acid (1R*,2R*,4R*)-(5RS)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-2-yl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 22 mg of rac-isobutyric acid (1R*,2R*,4R*)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester dissolved in 0.6 mL EtOH (evacuated 3 times with N2) were added 10 mg of 10 wt % Pd/C. The reaction mixture was stirred under a H2 atmosphere (balloon) for 1 h, filtered over a pad of celite and the cake was washed with EtOH and concentrated in vacuo to provide crude isobutyric acid (1R*,2R*,4R*)-(5RS)-2-(2-{[3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-2-yl ester as mixture of 2 diastereoisomeric racemates. Purification by CC using EtOAc/MeOH 2/1 yielded 5 mg of racemate A and 6 mg of racemate B, both as colorless oils.

Workup

  1. filtrationfiltered over a pad of celite
  2. washthe cake was washed with EtOH
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f3d7195b00241d3a1bc2d2c2881683e
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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