5-broMo-4,4-diMethyl-1,2,3,4-tetrahydroisoquinoline synthesis
- Product Name:5-broMo-4,4-diMethyl-1,2,3,4-tetrahydroisoquinoline
- CAS Number:1203684-57-4
- Molecular formula:C11H14BrN
- Molecular Weight:240.14
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Yield:1203684-57-4 0.8 g
Reaction Conditions:
Stage #1: 5-bromo-4,4-dimethyl-3,4-dihydroisoquinoline-1(2H)-onewith dimethylsulfide borane complex in tetrahydrofuran at 0; for 19 h;Reflux;
Stage #2: with methanol for 18 h;Reflux;
Steps:
103D 5-Bromo-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline
To a solution of 103C (1.0 g, 3.93 mmol) in dry THF (10 mL) at 0 °C, was added borane-dimethyl sulfide complex (1.12 mL, 11.81 mmol), the reaction mixture was slowly brought to rt, stirred for 1 h and then heated to reflux for 18 h. The solvent was removed and the residue was quenched with MeOH and heated to reflux for 18 h. The solvent was removed and the residue was dissolved in EtOAc, washed with H2O, brine, dried (Na2S04), filtered and concentrated to give 0.8 g of 103D as a white solid. The material was carried onto the next step without further purification. MS (ESI) m/z: 240.0 (M+H)+.
References:
WO2013/56034,2013,A1 Location in patent:Paragraph 003606
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