Isoquinolin-3-Amine → 5,6,7,8-Tetrahydroisoquinolin-3-amine

Using the method of Example 63, Step A, 75 mg of 3-aminoisoquinoline (7.73 mmoles) and 8.7 mg platinum oxide in 2 mL of trifluoroacetic acid was shaken under 40 psi of hydrogen for 3 h. The mixture was filtered and catalyst was washed with ethyl acetate. After concentrating the filtrate, the residue was dissolved in 10 mL of ethyl acetate and washed with 5 mL of saturated aquous sodium bicarbonate. The organic solution was dried (sodium sulfate), decanted, and concentrated to give a yellow syrup. Flash coumn chromatography on 19 g of silica gel, eluting with 600 mL of 50% ethyl acetate/hexane gave 26.5 mg (34% yield) of 3-amino-5,6,7,8-tetrahydroisoquinoline as a pale yellow solid.