Hydrochloric Acid → HCID 21990024, compound

HRID 597818Notes

Reaction equation

HRID 597818 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][C:14]([N:16]3[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17]3)=O)=[CH:9][C:4]=2[CH:3]=[CH:2]1.Cl.O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:16]3[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17]3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 21990164HCID 21990164, compound

Product 1

HCID 21990024HCID 21990024, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.39 g of 2-(2-(1-benzofuran-5-yl)ethoxy)-1-(3-hydroxy-1-pyrrolidinyl)-1-ethanone was dissolved in 14.0 ml of tetrahydrofuran. Thereafter, 14.4 ml of a tetrahydrofuran solution containing a 1 mol/l borane-tetrahydrofuran complex was added dropwise to the obtained solution while cooling on ice, and the obtained mixture was then stirred at a room temperature for 17 hours. Thereafter, 8.0 ml of 6 mol/l hydrochloric acid was added to the reaction mixture, and the obtained mixture was heated to reflux for 1 hour. After cooling, water and ethyl acetate were added to the reaction mixture. The pH of the obtained mixture was adjusted to pH 10 by addition of a 2 mol/l aqueous sodium hydroxide solution, and an organic layer was separated. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; chloroform:methanol=30:1 to 10:1), so as to obtain 0.96 g of an achromatic oil product, 1-(2-(2-(1-benzofuran-5-yl)ethoxy)ethyl)-3-pyrrolidinol.

Workup

  1. additionwas added dropwise to the obtained solution
  2. temperaturewhile cooling on ice
  3. temperaturethe obtained mixture was heated
  4. temperatureto reflux for 1 hour
  5. temperatureAfter cooling
  6. customan organic layer was separated
  7. washThe organic layer was successively washed with water
  8. dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
  9. distillationThereafter, the solvent was distilled away under a reduced pressure
  10. customThe residue was purified by column chromatography (eluent; chloroform:methanol=30:1 to 10:1)

Sources & evidence

ORD record
ord-6f2d3ef702cb4506ba7a77f827599314
Source dataset
uspto-grants-2011_03
Patent number
US07897594B2

Reaction notes

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