1-Amino-2-propanol → HCID 19036546, compound

HRID 264512Notes

Reaction equation

HRID 264512 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH:7]([CH2:13][C:14](=O)[CH3:15])[CH2:6]2.O.[NH2:18][CH2:19][CH:20]([OH:22])[CH3:21]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]1[N:18]([CH2:19][CH:20]([OH:22])[CH3:21])[C:14]([CH3:15])=[CH:13][C:7]=1[CH2:6]2

Participants

6

Reactant 3

HCID 41-Amino-2-propanolHCID 962WaterHCID 19036578HCID 19036578, compound

Product 1

HCID 19036546HCID 19036546, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 1.2 g of (RS)-5-methoxy-2-(2-oxopropyl)-1-indanone and 60 mg of p-toluenesulfonic acid in 70 ml of anhydrous toluene was heated on a water separator. A solution of 1.65 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). 1.17 g (82%) of (RS)-1-(6-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a yellow solid which was used without further crystallization 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-efeeed6a0dae4302a07394d2605bc476
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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