Hydrochloric Acid → HCID 24996754, compound

Participants

Reaction Steps

To a solution of 2-benzyl-6-(trifluoromethyl)-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one (0.820 g, 2.00 mmol) in 50 mL of dioxane was added 12N aqueous HCl (0.170 mL, 2.00 mmol) followed by 30% palladium on carbon (0.250 g) and the stirred mixture was hydrogenated under balloon pressure of hydrogen. After 45 minutes, additional 30% palladium on carbon (0.090 g) was added. After hydrogenating for an additional 1 hour, the mixture was filtered through a pad of silica gel, washing with EtOAc. The filtrate was washed with 5% aqueous NaHCO3 and the aqueous phase was back-extracted with EtOAc. The combined organic layers were diluted with Et2O and hexanes and washed with water and brine. The organic phase was concentrated under vacuum and the residue was chromatographed on silica gel (elution with 1:4 to 1:1 EtOAc/hexanes) to yield (rac)-(8R,10aS)-6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one as a white solid.

Provenance & Evidence