Reaction equation
[OH:1][C@@H:2]([CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)[CH2:22][CH2:21]1)[CH2:3][O:4][C:5]1[C:10]2[O:11][C:12]([C:14]([O:16]CC)=[O:15])=[CH:13][C:9]=2[CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].Cl>CO>[OH:1][C@@H:2]([CH2:19][N:20]1[CH2:21][CH2:22][CH:23]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)[CH2:24][CH2:25]1)[CH2:3][O:4][C:5]1[C:10]2[O:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=2[CH:8]=[CH:7][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl (S)-7-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)benzo(b)furan-2-carboxylate (5.2 g) in methanol (50 ml) was added 10% saturated aqueous sodium hydroxide solution (50 ml) and the mixture was refluxed under heating for 1 hr. The reaction mixture was made acidic (pH 1) with conc. hydrochloric acid and extracted with chloroform. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (4.0 g) as a brown oil.
Workup
- temperaturethe mixture was refluxed
- temperatureunder heating for 1 hr
- extractionextracted with chloroform
- washThe organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-049a1f55c1d3412fb30295ab1b671808
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196199B2
Linked notes
Loading…