Triphenylphosphine → tert-butyl 4-[1-(2-methoxy-2-oxoethyl)-1H-tetraazol-5-yl]piperidine-1-carboxylate

Participants

Reaction Steps

Triphenylphosphine (1.28 g, 4.89 mmol), DEAD (804 μL, 4.89 mmol), and methyl glycolate (378 μL, 4.89 mmol) were added to a solution of tert-butyl 4-(1H-tetraazol-5-yl)piperidine-1-carboxylate (619.7 mg, 2.447 mmol) in dichloromethane (20 mL). The reaction mixture was stirred for 16 h at rt and then concentrated under reduced pressure. Purification by MPLC (silica gel, 10-50% EtOAc/hexanes) afforded tert-butyl 4-[1-(2-methoxy-2-oxoethyl)-1H-tetraazol-5-yl]piperidine-1-carboxylate. ESI-MS calculated for C14H23N5O4: 325.36, found 348 (M+Na).

Provenance & Evidence