1-Amino-2-propanol → HCID 10633999, compound

HRID 264534Notes

Reaction equation

HRID 264534 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=O.O.[NH2:17][CH2:18][CH:19]([OH:21])[CH3:20]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:14][O:13][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5]1[N:17]([CH2:18][CH:19]([OH:21])[CH3:20])[CH:2]=[CH:3][C:4]=1[CH2:12]2

Participants

6

Reactant 3

HCID 41-Amino-2-propanolHCID 962WaterHCID 10560109HCID 10560109, compound

Product 1

HCID 10633999HCID 10633999, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 2 g of (RS)-2-(2-oxoethyl)-5-methoxy-1-indanone and 80 mg of p-toluenesulfonic acid in 90 ml of anhydrous toluene was heated on a water separator. A solution of 2.94 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 35 minutes, during which the solvent was reduced to a volume of 25 ml. The cooled reaction mixture was purified by column chromatography on silica gel (ethyl acetate/toluene 1:1). There were obtained 1.6 g (67%) of (RS)-1-(6-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol as a brown oil which was used directly in the next reaction.

Workup

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

Sources & evidence

ORD record
ord-dd76b94432484b3d98341f3b1fe3cbc6
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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