N-Hydroxyphthalimide → HCID 178475039, compound

Participants

Reaction Steps

A solution of 39.5 ml (0.2413 mol) of diethyl azodicarboxylate (95%) in 300 ml of tetrahydrofuran is added dropwise to a mixture of 36.13 g (0.2298 mol) of cis-4-acetaminocyclohexanol [Ber. Dtsch. Chem. Ges. 72, 995 (1939)], 37.49 g (0.2298 mol) of N-hydroxyphthalimide, 60.28 g of triphenylphosphine and 1500 ml of tetrahydrofuran at 20°-30° C., while stirring. After stirring at room temperature for 14 hours, in each case 20% of the amount of triphenylphosphine and diethyl azodicarboxylate originally employed is again added to the reaction mixture, stirring is continued for 6 hours and the reaction mixture is left to stand at room temperature for 2.5 days. The crystalline precipitate formed is filtered off and washed with tetrahydrofuran. The title compound thus obtained melts at 210°-213° C. The yield can be increased by further recrystallization or chromatography of the mother liquor.

Provenance & Evidence