Reacción #159573

Ecuación de reacción

(S)-tert-butyl (1-(4-bromophenyl)ethyl)carbamate

1,3-bis(diphenylphosphino)-propane

triethylamine

→

title compound ( D2 )

Rendimiento 176.2%

(S)-methyl 4-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate

Rendimiento 176.2%

Disolventes

N,N-dimethylformamide methanol

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   Lavadowashed with water (3×100 ml)
3. 3
   SecadoThe organic layer was dried over Na2SO4
4. 4
   Otroevaporated in vacuo
5. 5
   OtroThe residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 5:1

Procedimiento

A mixture of (S)-tert-butyl (1-(4-bromophenyl)ethyl)carbamate (D1) (9.20 g, 27.3 mmol), 1,3-bis(diphenylphosphino)-propane (2.25 g, 5.46 mmol), palladium (II) acetate (1.22 g, 5.46 mmol), and triethylamine (11.5 ml, 81.9 mmol) in N,N-dimethylformamide/methanol (60 ml/60 ml) was stirred at 80° C. overnight under carbon monoxide atmosphere. After cooling to room temperature, the mixture was diluted with ether (300 ml) and washed with water (3×100 ml). The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 5:1 to afford the title compound (D2) (6.72 g) as white solid.

Fuente