Aluminium lithium hydride → N-[2-({2-Amino-1-[1-(4-fluorophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide

A reaction vessel was charged with lithiumaluminium hydride (23.5 mg, 0.618 mmol) and dry tetrahydrofuran (1 mL). N-[2-({1-[1-(4-fluorophenyl)cyclobutyl]-2-nitroso-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide (49 mg, 0.103 mmol, cf. example 75) was added dropwise as a solution in dry tetrahydrofuran (1 mL) at 0° C. After the addition was completed the reaction mixture was stirred at room temperature for 1 h and then at 40-50° C. for 1 h. After cooling to room temperature the reaction mixture was poured on ice water (15 mL) and the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo. The crude product was purified by preparative HPLC (RP, acetonitrile, water). Yield: 1 mg (2.2 μmol, 2%)