Water → HCID 70008253, compound

Participants

Reaction Steps

(1R*,2R*,5S*,6R*)-2-Dibenzylamino-8-benzyl-6-(hydroxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Description 21; 400 mg, 0.78 mmol) was dissolved in tetrahydroftiran (10 mL) and treated with lithium aluminium hydride solution (800 μL, 1M, 0.8 mmol) in tetrahydrofuran. The resulting mixture was stirred for 16 hours, then a further portion of lithium aluminium hydride solution (200 μL, 1M, 0.8 mmol) in tetrahydrofuran was added. Stirred at 50° C. for 1 hour, then cooled, and water (40 μL) added, followed by 15% aqueous sodium hydroxide solution (40 μL), then water (120 μL). The suspension formed was filtered and the filtrate taken up in water (10 mL). This mixture was extracted with ethyl acetate (2×10 mL) and the extracts were dried (MgSO4), before being concentrated in vacuo. The gum remaining was purified by silica chromatography to give the title compound (295 mg, 0.59 mmol) as a gum.

Provenance & Evidence