تفاعل #71268

معادلة التفاعل

(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

المردود 89.5%

المذيبات

water

ethylacetate

EtOAc

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONadded
2. 2
   درجة الحرارةThe mixture was cooled in an ice bath
3. 3
   أخرىcame to room temperature
4. 4
   أخرىThe crude reaction mixture
5. 5
   workup.ADDITIONthe phases mixed
6. 6
   أخرىseparated
7. 7
   استخلاصThe aqueous layer was further extracted with EtOAc (×2)
8. 8
   أخرىCombined organics were dried
9. 9
   تركيزconcentrated before crystallisation of the product from ethylacetate/heptane mixture

الإجراء التجريبي

(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)

المصدر