반응 #71273

반응 방정식

(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

수율 108.0%

용매

water

ethylacetate

EtOAc

water

반응 조건

후처리

1. 1
   workup.ADDITIONadded
2. 2
   온도The mixture was cooled in an ice bath
3. 3
   기타came to room temperature
4. 4
   기타The crude reaction mixture
5. 5
   workup.ADDITIONthe phases mixed
6. 6
   기타separated
7. 7
   추출The aqueous layer was further extracted with EtOAc (×2)
8. 8
   기타Combined organics were dried
9. 9
   농축concentrated

실험 절차

(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)

출처