(7-bromo-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (7-bromo-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol (620 mg, 2.6 mmol) in N,N-dimethylformamide (5 mL) was added tert-butyldimethylsilyl chloride (580 mg, 3.8 mmol, Aldrich, Cat. No. 190550) and 1H-imidazole (260 mg, 3.8 mmol). The solution was stirred at r.t. overnight. The reaction solution was diluted with water, and extracted with AcOEt. The organic layer was washed with brine, dried over MgSO4. After filtration, the filtrate was concentrated to afford the desired compound which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=356.3. extracted with AcOEt The organic layer was washed with brine dried over MgSO4 After filtration the filtrate was concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 7-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (1.0 g, 3.7 mmol) in tetrahydrofuran (20 mL) was added 1.0 M of lithium tetrahydroaluminate in tetrahydrofuran (7.40 mL, 7.40 mmol, Aldrich Cat. No. 212776) dropwise at 0° C. The solution was stirred at 0° C. for 2 h. Water (0.3 mL), 15% NaOH aqueous solution (0.3 mL) and water (1.0 mL) were added dropwise in sequence to the reaction solution. The suspension was filtered through a pad of celite, and washed with ether. The filtrate was concentrated to afford the desired compound which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=242.2. dropwise at 0° C The suspension was filtered through a pad of celite washed with ether The filtrate was concentrated