Triphenylphosphine → Methyl cis-3-azidomethylcyclopentancarboxylate

Participants

Reaction Steps

To a mixture of methyl cis-3-hydroxymethylcyclopentancarboxylate (4.74 g, 30 mmol) in dry benzene (about 250 mL) was added triphenyl phosphine (7.86 g, 30 mmol), diethyl azodicarboxylate (5.22 g, 30 mmol) and hydrazoic acid (2.5 M in toluene, 14.0 mL, 35 mmol). The mixture was stirred at room temperature for about 16 h. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate and hexane was added. A precipitate formed on standing in about 2 h and was removed by filtration. The filtrate was concentrated and the residue was passed through a column of silica gel using chloroform as eluent. The appropriate fractions were combined and concentrated to give 2.6 g (47%) of methyl cis-3-azidomethyl-cyclopentancarboxylate.

Provenance & Evidence