Sodium cyanoborohydride → HCID 66679365, compound

Participants

Reaction Steps

7-Bromo-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine XVI was prepared from commercial available 7-bromo-6-fluoro-3,4-dihydro-1H-naphthalen-2-one XV. To a stirred solution of XV (0.10 g, 0.41 mmol) in 3 mL of MeOH was added NH4OAc, followed by NaCNBH3 (0.018 g) in one portion at ambient temperature. The reaction mixture was stirred at ambient temperature for 16 h. Removal of solvent under vacuum gave the crude product, which was partitioned between 2N Na2CO3 and CH2Cl2. The organic layer was separated and dried over MgSO4. The solvent was removed under vacuum and the so-obtained crude product was dissolved in 2 mL of CH2Cl2. To this solution was added TEA (0.12 mL) and (Boc)2O (90 mg, 0.41 mmol). The reaction mixture was stirred at rt overnight. Removal of the solvent under vacuum gave the crude product, which was purified by column to give the pure product XVII (119 mg, 84% over 2 steps). MS: calc'd (MH+) 344, exp (MH+) 344.

Provenance & Evidence