Réaction #71268

Équation de réaction

(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

Rendement 89.5%

Solvants

water

ethylacetate

EtOAc

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONadded
2. 2
   TempératureThe mixture was cooled in an ice bath
3. 3
   Autrecame to room temperature
4. 4
   AutreThe crude reaction mixture
5. 5
   workup.ADDITIONthe phases mixed
6. 6
   Autreseparated
7. 7
   ExtractionThe aqueous layer was further extracted with EtOAc (×2)
8. 8
   AutreCombined organics were dried
9. 9
   Concentrationconcentrated before crystallisation of the product from ethylacetate/heptane mixture

Mode opératoire

(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)

Source