Reacción #6044

Ecuación de reacción

benzyl alcohol

diphenylphosphoryl azide

3-methylenecyclobutane carboxylic acid

triethylamine

→

desired compound

Rendimiento 68.5%

Benzyloxycarbonyl-3-methylenecyclobutanamine

Rendimiento 68.5%

Disolventes

ether

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 15 h at 85° C.
2. 2
   Otrothe cooled reaction mixture
3. 3
   Lavadowashed with saturated aqueous NaHCO3
4. 4
   Secadosaturated aqueous NaCl, dried over MgSO4
5. 5
   Concentraciónconcentrated under reduced pressure

Procedimiento

To a stirred solution of 26.7 g (238 mmol) of 3-methylenecyclobutane carboxylic acid (Cripps, H. N.; Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 2723-2728) in 100 mL of toluene at 0° C. was added 36.4 mL (262 mmol) of triethylamine and then 72.1 g (262 mmol) of diphenylphosphoryl azide. The reaction mixture was then heated at 80° C., and after 1 h, 28.33 g (262 mmol) of benzyl alcohol was added. After 15 h at 85° C., the cooled reaction mixture was poured into 1 L of ether, washed with saturated aqueous NaHCO3, and then saturated aqueous NaCl, dried over MgSO4, and then concentrated under reduced pressure. Chromatography of the residue in three portions on 1400 g of silica gel with 80:20/hexane:EtOAc afforded 35.4 g (63%) of the desired compound.

Fuente