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

HRID 264479Notes

Reaction equation

HRID 264479 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([CH2:13][CH:14]=O)[C:9]2=O)=[CH:5][CH:4]=1.O.[NH2:17][CH2:18][CH:19]([OH:21])[CH3:20].[C:22]1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8]3[CH:13]=[C:14]([CH3:22])[N:17]([CH2:18][CH:19]([OH:21])[CH3:20])[C:9]=32)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 41-Amino-2-propanolHCID 962WaterHCID 1140Toluene2×HCID 10703357(RS)-2-(2-oxoethyl)-6-methoxy-1-indanone

Product 1

HCID 19036536(RS)-1-(7-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-olYield 65%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A solution of 1.8 g of (RS)-6-methoxy-2-(2-oxoethyl)-1-indanone and 70 mg of p-toluenesulfonic acid in 70 ml of anhydrous toluene was heated on a water separator. A solution of 2.48 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 90 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 (diethyl ether/hexane 7:3). 1.37 g (65%) of (RS)-1-(7-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a brown solid which was used directly in the next reaction.

Workup

  1. customThe cooled reaction mixture
  2. customwas purified by column chromatography on silica gel (diethyl ether/hexane 7:3)

Sources & evidence

ORD record
ord-1ff0fffa74c34d89a8ed1630c2d14800
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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