4-Nitrobenzoic Acid → HCID 67823507, compound

Participants

Reaction Steps

With stirring, a solution of 2 ml (0.012 mol) of diethyl azodicarboxylate (93%) in 10 ml of toluene is added dropwise at 5°-10° C. to a suspension of 2.15 g (0.01 mol) of cis-N-BOC-2-methyl-4-hydroxypiperidine (cf. Example 1b), 2.0 g (0.012 mol) of 4-nitrobenzoic acid and 3.15 g (0.012 mol) of triphenylphosphine in 30 ml of toluene. The reaction mixture is further stirred for 15 hours at room temperature and then filtered to remove precipitated diethyl hydrazinedicarboxylate. The filtrate is then concentrated under vacuum and the oily residue is purified by flash chromatography over silica gel using ethyl acetate:hexane (1:5). Concentration of the fractions containing the product gives the title compound as a crystalline residue which melts at 106°-108° C.

Provenance & Evidence