Boron trifluoride etherate → 6-(5-Bromo-2-chloro-benzyl)-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinoline

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).

1. customThe reaction was quenched by the addition of aq. NaHCO3
2. customThe volatiles were evaporated under reduced pressure
3. extractionthe resulting mixture was extracted with dichloromethane (2×50 mL)
4. washwashed with brine (10 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. custompurified by silica gel column chromatography

ORDレコード

ord-485388d5923a45ec9a2912adb9e746f3

出典データセット

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08163704B2