Sodium Azide → HCID 57545168, compound

Participants

Reaction Conditions

Reaction Steps

56.9 mg (0.87 mmol) of sodium azide are added to 200 mg (0.44 mmol) of (1S*,3S*,3aR*,8bS*)-6-(2-chloroethoxy)-3a-(4-chlorophenyl)-3-phenyl-2,3,3a,8b-tetrahydrocyclopenta[b]benzofuran-1,8b-(1H)-diol (Example 48A) in 4 ml of DMF under argon, and the mixture is heated at 100° C. overnight. After cooling and concentration, the residue is taken up in water and dichloromethane, the phases are separated, the aqueous phase is extracted twice with dichloromethane, and the combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. Gradient chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate) results in 190 mg (94% of theory) of the product.

Provenance & Evidence