Reaction #1121811

Reaction equation

m-CPBA

tert-butyl 5,6-dihydropyridine-1(2H)-carboxylate

sodium sulfite

sodium bicarbonate

→

tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Yield 99.0%

Solvents

DCM

DCM

Conditions

Workup

1. 1
   workup.WAITat room temperature for 3 hours
2. 2
   OtherThe organic layer was separated
3. 3
   Washwashed with brine
4. 4
   Dryingdried (sodium sulfate)
5. 5
   Concentrationconcentrated in vacuo

Procedure

A solution of m-CPBA (7.53 g, 32.7 mmol) in DCM (10 mL) was added to a solution of tert-butyl 5,6-dihydropyridine-1(2H)-carboxylate (5.00 g, 27.3 mmol) in DCM (20 mL) at 0° C. The reaction was stirred at 0° C. for 15 minutes and then at room temperature for 3 hours. Saturated sodium sulfite solution (20 mL) and saturated sodium bicarbonate solution (30 mL) was added. The organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated in vacuo to give tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (5.36 g, 99%) as oil.

Source