Ethanol → Ethyl 3-((2R)-2-{[(2 R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}propyl)-1H-indole-7-carboxylate

HRID 1351961Notes

Reaction equation

HRID 1351961 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:26])[CH2:9][NH:10][C@H:11]([CH3:25])[CH2:12][C:13]2[C:21]3[C:16](=[C:17]([C:22]([OH:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH2:32](O)[CH3:33]>>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:26])[CH2:9][NH:10][C@H:11]([CH3:25])[CH2:12][C:13]2[C:21]3[C:16](=[C:17]([C:22]([O:24][CH2:32][CH3:33])=[O:23])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 694577363-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carboxylic acid

Product 1

HCID 21098843Ethyl 3-((2R)-2-{[(2 R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}propyl)-1H-indole-7-carboxylateYield 93%

Conditions

Temperature
150 °C

Procedure

3-{(2R)-2-[2-(3-Chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carboxylic acid (50 mg, 0.134 mmol) is dissolved in ethanol (5 mL), and thereto are added conc. sulfuric acid (0.05 mL) and Molecular Sieves 4A powder (trade name, 0.3 g), and the mixture is heated at 150° C. for 16 hours. After cooling, the insoluble materials are removed by filtration, and a saturated aqueous sodium hydrogen carbonate solution is added to the filtrate. The mixture is evaporated under reduced pressure to remove ethanol, and the resultant is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over sodium sulfate, and concentrated. The residue is purified by silica gel column chromatography (chloroform/ethanol=4/1) to give the title compound (50 mg, yield: 93%).

Workup

  1. temperatureAfter cooling
  2. customthe insoluble materials are removed by filtration
  3. additiona saturated aqueous sodium hydrogen carbonate solution is added to the filtrate
  4. customThe mixture is evaporated under reduced pressure
  5. customto remove ethanol
  6. extractionthe resultant is extracted with ethyl acetate
  7. washThe organic layer is washed with a saturated brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue is purified by silica gel column chromatography (chloroform/ethanol=4/1)

Sources & evidence

ORD record
ord-ee0a22b04b554d2d8dcc14dd171b1ee7
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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