Sodium Hydroxide → (1R*,2R*,3S*,5S*,6R*)-2-Benzylamino-8-benzyl-3-fluoro-1-phenyl-6-(hydroxymethyl)-8-azabicyclo[3.2.1]octane

Participants

Reaction Steps

(1R*,2R*,3S*,5S*,6R*)-2-Benzylamino-8-benzyl-3-fluoro-1-phenyl-6-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octane (Description 36b; 651 mg, 1.3 mmol) was dissolved in tetrahydrofuran (10 mL) and then treated with a solution of lithium triethylborohydride in tetrahydrofuran (4 mL, 1M, 4 mmol). The solution was stirred at room temperature for 1 hour, then poured into aqueous sodium hydroxide solution (50 mL, 1M). The suspension formed was extracted with ethyl acetate (2×100 mL) and the extracts were dried (MgSO4). Concentration in vacuo gave a gum which was purified by silica chromatography to give the title compound (476 mg, 1.1 mmol).

Provenance & Evidence