Hydrochloric Acid → 1-((3R,4R)-3-amino-4-methoxypyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone
Reaction equation
[CH3:1][O:2][C@H:3]1[C@H:7]([NH:8]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6][N:5]([C:28](=[O:41])[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=2)[CH2:4]1.Cl>C(OCC)C>[NH2:8][C@H:7]1[C@H:3]([O:2][CH3:1])[CH2:4][N:5]([C:28](=[O:41])[CH2:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][C:37]([F:38])([F:39])[F:40])=[CH:34][CH:35]=2)[CH2:6]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-((3R,4R)-3-Methoxy-4-(tritylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone (0.65 g) was dissolved in diethyl ether (5 mL), followed by addition of 5 M hydrochloric acid (5 mL), and the mixture was stirred at room temperature for 17 h. The layers were separated, and the aqueous layer was washed with diethyl ether, 1 M aqueous sodium hydroxide was added to make it basic, and the mixture was extracted with chloroform. The organic layer was dried with anhydrous magnesium sulfate, the desiccant was removed by filtration, and then the filtrate was concentrated under reduced pressure to obtain the title compound (0.35 g).
Workup
- customThe layers were separated
- washthe aqueous layer was washed with diethyl ether, 1 M aqueous sodium hydroxide
- additionwas added
- extractionthe mixture was extracted with chloroform
- dry with materialThe organic layer was dried with anhydrous magnesium sulfate
- customthe desiccant was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-7e5e8d755cf04ed3aa377cd520e071b6
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08044068B2
Reaction notes
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