Reacción #71273

Ecuación de reacción

(S)-5-bromo-2,3-dihydro-1H-inden-2-amine((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate

potassium carbonate

benzyl chloroformate

→

(S)-benzyl 5-bromo-2,3-dihydro-1H-inden-2-ylcarbamate

Rendimiento 108.0%

Disolventes

water

ethylacetate

EtOAc

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONadded
2. 2
   TemperaturaThe mixture was cooled in an ice bath
3. 3
   Otrocame to room temperature
4. 4
   OtroThe crude reaction mixture
5. 5
   workup.ADDITIONthe phases mixed
6. 6
   Otroseparated
7. 7
   ExtracciónThe aqueous layer was further extracted with EtOAc (×2)
8. 8
   OtroCombined organics were dried
9. 9
   Concentraciónconcentrated

Procedimiento

(S)-5-bromo-2,3-dihydro-1H-inden-2-amine((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate (18.47 mmol, 8.21 g) was dissolved in EtOAc (30 mL)/water (30 mL) and potassium carbonate (55.4 mmol, 7.66 g) added. The mixture was cooled in an ice bath and benzyl chloroformate (20.32 mmol, 2.89 mL, 3.47 g) added dropwise. Stirring was continued overnight during which time the reaction came to room temperature. The crude reaction mixture was diluted with water and ethylacetate and the phases mixed and separated. The aqueous layer was further extracted with EtOAc (×2). Combined organics were dried and concentrated to give (S)-benzyl 5-bromo-2,3-dihydro-1H-inden-2-ylcarbamate as a colourless solid (6.89 g, 108%). 1H NMR (400 MHz, CDCl3) δ 2.79 (m, 2H) 3.26 (m, 2H) 4.53 (bm, 1H) 4.93 (bm, 1H) 5.10 (bs, 2H) 7.07 (m, 1H) 7.26-7.37 (m, 7H)

Fuente