N-Hydroxyphthalimide → HCID 178454077, compound

Participants

Reaction Steps

4.1 ml (0.0244 mol) of diethyl azodicarboxylate (93%) are added dropwise to a mixture of 5 g (0.0232 mol) of trans-4-(N-BOC-amino)-cyclohexanol (cf. Example 1c), 3.8 g (0.0232 mol) of N-hydroxyphthalimide, 6.1 g (0.0232 mol) of triphenylphosphine and 100 ml of tetrahydrofuran at 20°-30° C. The reaction mixture is further stirred at room temperature for 15 hours and then evaporated in vacuo. To separate off the diethyl 1,2-hydrazinc dicarboxylate and triphenylphosphine oxide, the oily residue is dissolved in ethyl acetate, the solution is cooled to 0° C. and filtered, the filtrate is evaporated and the same operation is repeated once more, but using diethyl ether. The residue obtained after evaporation of the diethyl ether is purified by means of flash chromatography on silica gel using ethyl acetate/hexane mixtures (1:2 and 1:1). After evaporation of the product-containing fractions, the title compound is obtained as a crystalline residue, m.p. 134°-135° C.

Provenance & Evidence