Reacción #92710

Ecuación de reacción

carbon monooxide

1,3-bis(diphenylphosphino)propane

tert-butyl[(1S)-1-(3-bromophenyl)ethyl]carbamate

1,3-bis(diphenylphosphino)propane

triethylamine

→

methyl 3-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}benzoate

Rendimiento 151.2%

Disolventes

methanol

DMF

ethyl acetate

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGWhile stirring at room temperature
2. 2
   workup.STIRRINGby stirring at 80° C. overnight under a carbon monooxide atmosphere
3. 3
   workup.STIRRINGby stirring at 80° C. overnight
4. 4
   Otroa layer separation operation
5. 5
   LavadoThe organic layer was washed with saturated brine
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Otrothe solvent was evaporated under reduced pressure
8. 8
   OtroThe obtained residue was purified by silica gel column chromatography

Procedimiento

To 820 mg of tert-butyl[(1S)-1-(3-bromophenyl)ethyl]carbamate were added 113 mg of 1,3-bis(diphenylphosphino)propane, 62 mg of palladium acetate, 0.84 ml of triethylamine, 8 ml of DMF, and 12 ml of methanol, followed by stirring at room temperature for 1 hour. While stirring at room temperature, carbon monooxide was intaken for 10 minutes, followed by stirring at 80° C. overnight under a carbon monooxide atmosphere. 113 mg of 1,3-bis(diphenylphosphino)propane and 62 mg of palladium acetate were added thereto, followed by stirring at 80° C. overnight. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 577 mg of methyl 3-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}benzoate.

Fuente