반응 #71268

반응 방정식

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

potassium carbonate

benzyl chloroformate

→

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

수율 89.5%

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 before crystallisation of the product from ethylacetate/heptane mixture

실험 절차

(R)-5-bromo-2,3-dihydro-1H-inden-2-amine((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate (12.56 mmol, 5.58 g) was dissolved in EtOAc (30 mL)/water (30 mL) and potassium carbonate (37.7 mmol, 5.21 g) added. The mixture was cooled in an ice bath and benzyl chloroformate (13.81 mmol, 1.964 mL, 2.356 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 before crystallisation of the product from ethylacetate/heptane mixture to give (R)-benzyl 5-bromo-2,3-dihydro-1H-inden-2-ylcarbamate as colourless needles (3.89 g, 89%). 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