Reaction #351632

Reaction equation

(S)-1-amino-2-propanol

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

water

→

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

Yield 63.0%

Solvents

toluene

toluene

Conditions

Workup

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

Procedure

A solution of 2 g of (RS)-2-(2-oxoethyl)-6-methoxy-1-indanone and 80 mg of p-toluenesulfonic acid in 70 ml of anhydrous toluene was heated on a water separator. A solution of 2.94 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 1:1). 1.5 g (63%) of (S)-1-(7-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a solid with m.p. 74°.

Source