1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Azidomethyl-2-(3-methyl-butyryl)-pyridine

Participants

Reaction Conditions

Reaction Steps

Add DBU (240 mg, 1.55 mmol) to a solution of 5-hydroxymethyl-2-(3-methyl-butyryl)-pyridine (250 mg, 1.29 mmol) and diphenylphosphorylazide (430 mg, 1.55 mmol) in anhydrous toluene (10 mL) at 0° C. Stir at 0° C. for 30 min, warm to room temperature and stir for 4 h. Dilute with EtOAc and water. Extract the aqueous phase twice with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (9:1) to provide the desired intermediate (300 mg, 99%). MS (ES+) m/z: 219 (M+H)+.

Provenance & Evidence