Sodium cyanoborohydride → 9-{[3-(5-fluoro-1H-indol-3-yl)propyl]amino}-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

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Reaction Steps

To a mixture of 9-amino-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one (46) (130 mg, 0.596 mmol), 3-(5-fluoro-1H-indol-3-yl)propanal ((2), 113 mg, 0.596 mmol) in acetic acid (70 μl) and methanol (20 ml) was added NaBH3CN (75 mg, 1.19 mmol) in portions. The resulting mixture was stirred for 2 hr. The solvent was removed in vacuo and the residue was dissolved in methylene chloride. The organic solution was washed with 1N NaOH and saturated NaCl before being dried over with Na2SO4. Concentration of organic solution gave the crude compound, which was purified on silica gel (100% EtOAc) to give the desired compound, which was treated with 1 equivalent of etherate HCL to form HCl salt for title compound. MS (APPI) m/z 394.4.

Provenance & Evidence