تفاعل #71273

معادلة التفاعل

(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

المردود 108.0%

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

الإجراء التجريبي

(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)

المصدر