1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide

Temperature

0 °C

2-Aminoindan hydrochloride (5.16 g, 30 mmol, Sigma-Aldrich Company Ltd) was suspended in dry dichloromethane (100 ml), and cooled with stirring under argon to 0° C. To the suspension was added 1,8-diazabicyclo[5.4.0]undec-7-ene (3 eq., about 14 ml, about 90 mmol) followed by the dropwise addition of isopropylsulfonyl chloride (6.8 ml, 60 mmol). The cooling bath was removed and the mixture stirred at room temperature for 1 h. The reaction mixture was washed with 1 M hydrochloric acid (2×50 ml). The organic layer was separated, dried over sodium sulphate and evaporated in vacuo (ie under reduced pressure) to give a yellow oil (11.8 g). The crude product was purified by chromatography on a 50 g Isolute™ Flash silica-gel column eluting from 20-50% ethyl acetate in petroleum ether to give the title compound as a colourless solid (6.88 g, 96%).

1. temperaturecooled
2. customThe cooling bath was removed
3. stirringthe mixture stirred at room temperature for 1 h
4. washThe reaction mixture was washed with 1 M hydrochloric acid (2×50 ml)
5. customThe organic layer was separated
6. dry with materialdried over sodium sulphate
7. customevaporated in vacuo (ie under reduced pressure)

ORD record

ord-d6fad73eb59c4ace888b9d8f065a95ac

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572819B2