Reaction #351630

Reaction equation

(S)-1-amino-2-propanol

(RS)-2-(2-oxoethyl)-6-fluoro-1-indanone

water

→

(S)-1-(7-fluoro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

Yield 65.4%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   OtherThe cooled reaction mixture
2. 2
   Otherwas purified by column chromatography on silica gel (ethyl acetate/toluene 2:3)

Procedure

A solution of 1.92 g of (RS)-2-(2-oxoethyl)-6-fluoro-1-indanone and 80 mg of p-toluenesulfonic acid in 90 ml of anhydrous toluene was heated on a water separator. A solution of 3.0 g of (S)-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 30 minutes, during which the solvent was reduced to a volume of 20 ml. The cooled reaction mixture was purified by column chromatography on silica gel (ethyl acetate/toluene 2:3). 1.51 g (65%) of (S)-1-(7-fluoro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a brown oil.

Source