Boron trifluoride etherate → 6-(5-Bromo-2-chloro-benzyl)-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinoline
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:29])=[C:6]([CH:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:15][CH2:14][CH2:13]3)O)[CH:7]=1.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:29])=[C:6]([CH:7]=1)[CH2:8][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[CH2:15][CH2:14][CH2:13]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To an ice cold solution of (5-bromo-2-chloro-phenyl)-[1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinolin-6-yl]-methanol (2.2 g, 4.7 mmol) in dichloromethane (50 mL) was added Et3SiH (3.7 mL, 23.3 mmol) followed by BF3.OEt2 (1.5 mL, 11.6 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was quenched by the addition of aq. NaHCO3. The volatiles were evaporated under reduced pressure; the resulting mixture was extracted with dichloromethane (2×50 mL), washed with brine (10 mL), dried over sodium sulfate, concentrated and purified by silica gel column chromatography to give 6-(5-Bromo-2-chloro-benzyl)-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinoline (1.48 g).
Workup
- customThe reaction was quenched by the addition of aq. NaHCO3
- customThe volatiles were evaporated under reduced pressure
- extractionthe resulting mixture was extracted with dichloromethane (2×50 mL)
- washwashed with brine (10 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- custompurified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-4ca9094c1a90406dbae4f9f4e91e9e67
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466114B2
Reaction notes
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