Hydrochloric Acid → (3aR, 7R,7aR)-4,4-diphenyl-7-fluoroperhydroisoindole hydrochloride

Participants

Reaction Conditions

Reaction Steps

A solution of 2.25 g of (3aR,7R,7aR)-2-t-butoxycarbonyl-4,4-diphenyl-7-fluoroperhydroisoindole in 25 cm3 of dioxane is treated with a 5.8N solution of hydrochloric acid in dioxane and stirred for 2 hours at 20° C. and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is concentrated by adding 100 cm3 of isopropyl oxide, the solid is filtered and dried to give 1.8 g of (3aR,7R,7aR)-4,4-diphenyl-7-fluoroperhydroisoindole hydrochloride, in the form of a cream-colored powder. Proton NMR spectrum (DMSO-d6): 1.0-1.35 (mt, 1H of CH2 in 6); 4.9 (broad d, J=50, 1H, CHF); 7.1 to 7.5 (mt, 14H, aromatics); 9.05 and 9.9 (2 mf, 2×1H, NH2+).

Provenance & Evidence