Diethyl Ether → benzyl N-(5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate

To a vigorously stirred solution of 5-bromo-2,3-dihydro-1H-inden-1-amine (8.54 g, 40.3 mmol) and potassium carbonate (11.1 g, 80 mmol) in water (100 mL) and ethyl acetate (100 mL) was added benzyl chloroformate (7.56 g, 44.3 mmol). The reaction was stirred at rt overnight before being diluted with water (200 mL) and dichloromethane (200 mL). The organic phase was collected and the aqueous phase was extracted once more with dichloromethane (100 mL). The clear colourless organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford a white solid. The material was co-evaporated once with diethyl ether and the residue was triturated with diethyl ether. The white solid was collected by filtration and dried on air to afford the title compound as a white solid (11.5 g, 82%). MS (ESI): m/z [M+H]+ 347.0

1. customThe organic phase was collected
2. extractionthe aqueous phase was extracted once more with dichloromethane (100 mL)
3. dry with materialThe clear colourless organic layers were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customto afford a white solid
7. customthe residue was triturated with diethyl ether
8. filtrationThe white solid was collected by filtration
9. customdried on air

ORD record

ord-4acdf977ef684dc1841282fcb0655c48

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633237B2