Reaction #309430

Reaction equation

toluenesulfonyl chloride

tert-butyl 4-[(2-benzoylhydrazino)carbonyl]piperidine-1-carboxylate

THF

→

tert-butyl 4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate

Yield 99.8%

Solvents

triethylamine

Conditions

Workup

1. 1
   OtherThe reaction liquid
2. 2
   Concentrationwas concentrated under reduced pressure
3. 3
   Otherthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Procedure

To a mixture of tert-butyl 4-[(2-benzoylhydrazino)carbonyl]piperidine-1-carboxylate (3.00 g) and THF (60 mL) were added triethylamine (7.2 mL) and toluenesulfonyl chloride (4.94 g), followed by stirring at 50° C. overnight. The reaction liquid was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain tert-butyl 4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate (2.84 g) as a colorless oily sub stance.

Source