Triphenylphosphine → HCID 19094408, compound

Participants

Reaction Steps

To a stirred solution of 3-(t-butoxycarbonylamino)-N-(2-cyanoethyl)propionamide (4.6 mmol) in THF (40 mL) under nitrogen is added triphenylphosphine (4.6 mmol). The solution is cooled to 0° and treated with diethyl azodicarboxylate (DEAD, 2.4 mmol) followed by trimethylsilyl azide (2.4 mmol). The solution is warmed up to room temperature and stirred for 18 hours. One additional equivalent of triphenyl phosphine (4.6 mmol), DEAD (2.4 mmol) and trimethylsilyl azide (2.4 mmol) are added and stirring is continued for 3 days. The solution is cooled to 0°. Ceric ammonium nitrate (0.2 L; 10% aqueous solution) is added dropwise. After 20 minutes of stirring, extraction is carried out with methylene chloride. The organic extract is dried over anhydrous sodium sulfate, then concentrated in vacuo. The residue is purified by chromatography to give 3-[5-(2-t-butoxycarbonylamino-ethyl)-tetrazol-1-yl]propionitrile.

Provenance & Evidence