Water → HCID 57129670, compound

Participants

Reaction Steps

3-(5-Amino-2-methoxyphenyl)-8-tert-butoxycarbonyl-8-azabicyclo[3.2.1]octane (D4, 0.385 g, 1.16 mmol) was dissolved in dry THF (30 ml) with stirring and was treated with lithium aluminium hydride (0.088 g, 2.32 mmol) under argon. The reaction mixture was then heated to reflux. After 2 h and 4 h, further amounts of lithium aluminium hydride (0.132 g, 3.48 mmol) were added. Reflux was then maintained for a further 4 h, before the reaction mixture was allowed to cool. Water (0.352 ml) was then added, followed by 10% NaOH (0.528 ml) and water (0.880 ml). The mixture was then stirred for 0.5 h before being filtered through kieselguhr. The filter pad was then washed with THF (20 ml) and the filtrate evaporated under reduced pressure to give the title compound as a brown solid (0.242 g, 85%).

Provenance & Evidence