Water → (R)-1-(7-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

HRID 264394Notes

Reaction equation

HRID 264394 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([CH3:13])=[CH:9][CH:10]=2)[C:5]1=O.O.[NH2:16][CH2:17][C@H:18]([OH:20])[CH3:19]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:13][C:8]1[CH:7]=[C:6]2[C:11]([CH2:12][C:4]3[CH:3]=[CH:2][N:16]([CH2:17][C@H:18]([OH:20])[CH3:19])[C:5]=32)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 439938(2R)-1-aminopropan-2-olHCID 10535615(RS)-2-(2-oxoethyl)-6-methyl-1-indanone

Product 1

HCID 53971660(R)-1-(7-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-olYield 79.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 2.82 g of (RS)-2-(2-oxoethyl)-6-methyl-1-indanone and 100 mg of p-toluenesulfonic acid in 100 ml of anhydrous toluene was heated on a water separator. A solution of 4.51 g of (R)-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/toluene 1:1). 2.7 g (79%) of (R)-1-(7-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a brown-green oil.

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-12e9121970dc4dc0a043d140b86a83ea
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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