Benzyl Alcohol → HCID 57069049, compound

Participants

Reaction Conditions

Reaction Steps

[1R,8S,9aR] 5-Methoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene-1-carboxylic acid (0.74 g, 2.3 mmol), from Step 5, and triethylamine (0.32 mL, 2.3 mmol) are dissolved in 16 mL of toluene and 0.55 mL (2.5 mmol) of diphenylphosphoryl azide is added. The mixture is heated at 80° C. for 2.5 hours then 0.5 mL (4.8 mmol) of benzyl alcohol is added and heating is continued at 80° C. for an additional 3 hours and at 65° C. for 15 hours. The mixture is cooled and concentrated under reduced pressure and 25 mL of diethyl ether is added. The solution is washed with 10 mL of 1N aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The product is purified by chromatography on silica gel to give the title compound.

Provenance & Evidence