Reacción #685169

Ecuación de reacción

triethylamine

acetaldoxime

N-chlorosuccinimide

tert-butyl 4-ethynyl-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate

→

tert-Butyl 4-(3-methyl-5-isoxazolyl)-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate

Disolventes

chloroform

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 4 h
2. 2
   Concentraciónconcentrated to dryness under reduced pressure
3. 3
   OtroThe residue was chromatographed on a silica gel column, with a gradient of 2:1 hexane/ethyl acetate to 2:1 ethyl acetate/hexane
4. 4
   Otroto give first
5. 5
   Otrorecovered

Procedimiento

To a solution of acetaldoxime (65 mg, 1.1 mmol) in 15 mL of chloroform were added 2 drops of pyridine, followed by N-chlorosuccinimide (146 mg, 1.1 mmol). After stirring the cloudy mixture for 1 h at ambient temperature, tert-butyl 4-ethynyl-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate (233 mg, 1.00 mmol) was added in 2 mL of chloroform, followed by drop-wise addition of triethylamine (0.175 mL, 1.25 mmol). The mixture was stirred at ambient temperature for 4 h and then concentrated to dryness under reduced pressure. The residue was chromatographed on a silica gel column, with a gradient of 2:1 hexane/ethyl acetate to 2:1 ethyl acetate/hexane, to give first recovered starting material, then tert-butyl 4-(3-methyl-5-isoxazolyl)-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate (100 mg, 40%).

Fuente