Reaction #71273

Reaction equation

(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

Yield 108.0%

Solvents

water

ethylacetate

EtOAc

water

Conditions

Workup

1. 1
   workup.ADDITIONadded
2. 2
   TemperatureThe mixture was cooled in an ice bath
3. 3
   Othercame to room temperature
4. 4
   OtherThe crude reaction mixture
5. 5
   workup.ADDITIONthe phases mixed
6. 6
   Otherseparated
7. 7
   ExtractionThe aqueous layer was further extracted with EtOAc (×2)
8. 8
   OtherCombined organics were dried
9. 9
   Concentrationconcentrated

Procedure

(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)

Source