反応 #71268

反応方程式

(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

収率 89.5%

溶媒

water

ethylacetate

EtOAc

water

反応条件

後処理

1. 1
   workup.ADDITIONadded
2. 2
   温度The mixture was cooled in an ice bath
3. 3
   その他came to room temperature
4. 4
   その他The crude reaction mixture
5. 5
   workup.ADDITIONthe phases mixed
6. 6
   その他separated
7. 7
   抽出The aqueous layer was further extracted with EtOAc (×2)
8. 8
   その他Combined organics were dried
9. 9
   濃縮concentrated before crystallisation of the product from ethylacetate/heptane mixture

実験手順

(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)

出典