1-Amino-2-propanol → (RS)-1-(5-chloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

HRID 264477Notes

Reaction equation

HRID 264477 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:13])[C:5]1=O.O.[NH2:16][CH2:17][CH:18]([OH:20])[CH3:19]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:13][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH2:12][C:4]1[CH:3]=[CH:2][N:16]([CH2:17][CH:18]([OH:20])[CH3:19])[C:5]=12

Participants

6

Reactant 3

HCID 41-Amino-2-propanolHCID 962WaterHCID 19036358(RS)-2-(2-oxoethyl)-4-chloro-1-indanone

Product 1

HCID 19036567(RS)-1-(5-chloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-olYield 59.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 2.08 g of (RS)-2-(2-oxoethyl)-4-chloro-1-indanone and 80 mg of p-toluenesulfonic acid in 70 ml of anhydrous toluene was heated on a water separator. A solution of 3.0 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 the solvent was reduced to a volume of 20 ml. The cooled reaction mixture was purified by column chromatography on silica gel (ethyl acetate/hexane 1:2). 1.47 g (59%) of (RS)-1-(5-chloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a brown oil.

Workup

  1. customThe cooled reaction mixture
  2. customwas purified by column chromatography on silica gel (ethyl acetate/hexane 1:2)

Sources & evidence

ORD record
ord-e80ae4228bca4e1c9cc80d5fbbf5f437
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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