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

Participants

Reaction Conditions

Reaction Steps

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 (14 g, 92 mmol) followed by the dropwise addition of isopropylsulfonyl chloride (8.56 g, 60 mmol). The cooling bath was removed and the mixture stirred at room temperature for 1 h. The reaction mixture was diluted with dichloromethane (50 ml) and washed with 1 M hydrochloric acid (2×50 ml). The organic layer was separated, dried over sodium sulphate and evaporated 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 40-60° C. petroleum ether to give the title compound as a pale yellow solid (6.88 g, 96%); 1H-NMR (400 MHz, CDCl3) δ 1.39 (6H, d, J=7 Hz), 2.91 (2H, m), 3.18 (1H, m), 3.31 (2H, m), 4.31 (2H, m), 7.21 (4H, m).

Provenance & Evidence