1-Amino-2-propanol → HCID 19036428, compound

HRID 264463Notes

Reaction equation

HRID 264463 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[NH2:30][CH2:31][CH:32]([OH:34])[CH3:33]>C1(C)C=CC=CC=1>[CH3:14][O:13][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:15][CH3:16])[C:5]1[N:30]([CH2:31][CH:32]([OH:34])[CH3:33])[CH:2]=[CH:3][C:4]=1[CH2:12]2

Participants

6

Reactant 4

HCID 41-Amino-2-propanolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 19036555HCID 19036555, compound

Product 1

HCID 19036428HCID 19036428, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2 g of (RS)-2-(2-oxoethyl)-5,6-dimethoxy-1-indanone and 80 mg of p-toluenesulfonic acid in 70 ml of anhydrous toluene was heated on a water separator. A solution of 2.56 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 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). 0.91 g (40%) of (RS)-1-(1,4-dihydro-6,7-dimethoxy-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol was obtained as an oil.

Workup

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

Sources & evidence

ORD record
ord-bb7d833874b74efd94e1fbf43c0ff28f
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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