Hydrochloric Acid → 4-(3-Amino-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile, hydrochloride

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Reaction Steps

156AF03-217 (252 mg, 0.912 mmol) was dissolved in methanol (25 mL). Ammonium acetate (702 mg, 9.12 mmol) and sodium cyanoborohydride (57.3 mg, 0.912 mmol) were added together with some molecular sieves (3 Å). This mixture was allowed to react at rt for 60 hours. Hydrochloric acid (2 M) was added until pH<2 and the mixture was washed with ethyl acetate (2×25 mL). The aqueous layer was made alkaline with sodium hydroxide and extracted with ethyl acetate (3×30 mL). The combined organic layers were evaporated to dryness and purified by ion-exchange (SCX) to give 90 mg (36%) of the title compound.

Provenance & Evidence