Water → (2R,4S)-2-Ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinolin-4-ylamine
Reaction equation
O.CC(C)([O-])C.[Na+].CS(O)(=O)=O.[CH2:13]([C@@H:15]1[CH2:24][C@H:23]([NH2:25])[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[NH:16]1)[CH3:14]>C1(C)C=CC=CC=1>[CH2:13]([C@@H:15]1[CH2:24][C@H:23]([NH2:25])[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)[NH:16]1)[CH3:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Water (0.1 ml) and sodium tert-butoxide (212 mg) were added to a solution of (2R,4S)-2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinolin-4-ylamine methane-sulfonate (500 mg) in toluene (2.5 ml) and the mixture was stirred at 80° C. for an hour. Thereto was added water (2.5 ml) and the mixture was stirred at 80° C. for 1.5 hours. The reaction mixture was cooled to room temperature and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo to give the titled compound.
Workup
- stirringthe mixture was stirred at 80° C. for 1.5 hours
- temperatureThe reaction mixture was cooled to room temperature
- customthe organic layer was separated
- washwashed with a saturated brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-436e109558f14a2ba784858de49a5e77
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084611B2
Reaction notes
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