1-Amino-2-propanol → (RS)-1-(7-isobutoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

HRID 264418Notes

Reaction equation

HRID 264418 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:9][CH:10]=2)[C:5]1=O.O.[NH2:20][CH2:21][CH:22]([OH:24])[CH3:23]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:14]([O:13][C:8]1[CH:7]=[C:6]2[C:11]([CH2:12][C:4]3[CH:3]=[CH:2][N:20]([CH2:21][CH:22]([OH:24])[CH3:23])[C:5]=32)=[CH:10][CH:9]=1)[CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 41-Amino-2-propanolHCID 962WaterHCID 19036556(RS)-2-(2-oxoethyl)-6-isobutoxy-1-indanone

Product 1

HCID 19036579(RS)-1-(7-isobutoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-olYield 57%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 2.3 g of (RS)-2-(2-oxoethyl)-6-isobutoxy-1-indanone and 70 mg of p-toluenesulfonic acid in 70 ml of anhydrous toluene was heated on a water separator. A solution of 2.93 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 (ethyl acetate/hexane 1:4). 1.52 g (57%) of (RS)-1-(7-isobutoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a red oil.

Workup

  1. customThe cooled reaction mixture
  2. customwas purified by column chromatography on silica gel (ethyl acetate/hexane 1:4)

Sources & evidence

ORD record
ord-d5545add6dd047a28dc898d28e4ca664
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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