Hydrochloric Acid → 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 dihydrochloride

HRID 220295Notes

Reaction equation

HRID 220295 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.[ClH:37]>CCOC(C)=O>[ClH:37].[ClH:37].[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[CH:18]=[C:19]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90876343HCID 90876343, compound

Product 1

HCID 131729783rac-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 dihydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

86 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 were dissolved in 2 mL EtOAc, the solution was cooled with an ice bath and 1 mL of 3M HCl in EtOAC was added. The reaction mixture was evaporated to dryness without heating to give the desired 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 dihydrochloride.

Workup

  1. temperaturethe solution was cooled with an ice bath
  2. customThe reaction mixture was evaporated to dryness
  3. temperaturewithout heating

Sources & evidence

ORD record
ord-c6cc3dde65c543a58007640c55bc2731
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

Loading…