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

HRID 264520Notes

Reaction equation

HRID 264520 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[CH3:13])[C:5]1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[NH2:27][CH2:28][CH:29]([OH:31])[CH3:30]>C1(C)C=CC=CC=1>[CH3:13][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:27]([CH2:28][CH:29]([OH:31])[CH3:30])[C:5]=12

Participants

6

Reactant 4

HCID 41-Amino-2-propanolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 19036491(RS)-2-(2-oxoethyl)-4-methyl-1-indanone

Product 1

HCID 19036420(RS)-1-(5-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-olYield 28%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1.9 g of (RS)-2-(2-oxoethyl)-4-methyl-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 (diethyl ether/hexane 7:3). 0.63 g (28%) of (RS)-1-(5-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol was obtained as a white 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-8eba10ee2e7140c0afe87c4872f98c5f
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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