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 (0.6 ml) and sodium tert-butoxide (1.27 g) were added to a solution of (2R,4S)-2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinolin-4-ylamine methane-sulfonate (3 g) in toluene (15 ml) and the mixture was stirred at 80° C. for an hour, then water (15 ml) was added, and the mixture was further stirred at 80° C. for an hour. 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 further stirred at 80° C. for an hour
- 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-e0d6f2adb3a242f3a6b0e74ced62643d
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084611B2
Reaction notes
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