1-Amino-2-propanol → (RS)-1-(6,7-dichloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

Participants

Reaction Steps

A solution of 2.0 g of (RS)-2-(2-oxoethyl)-5,6-dichloro-1-indanone and 70 mg of p-toluenesulfonic acid in 70 ml of anhydrous toluene was heated on a water separator. A solution of 2.47 g of (RS)-1-amino-2-propanol in 20 ml of anhydrous toluene was added dropwise to the boiling solution over a period of 5 minutes. Subsequently, the mixture was boiled for an additional 45 minutes, during which time the solvent was reduced to a volume of 20 ml. The cooled reaction mixture was purified by column chromatography on silica gel (diethyl ether/hexane 4:1). 0.62 g (27%) of (RS)-1-(6,7-dichloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol was obtained as a brown oil.

Provenance & Evidence