Hydrochloric Acid → HCID 21990024, compound

HRID 1092770Notes

Reaction equation

HRID 1092770 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

In 14.0 mL of tetrahydrofuran was dissolved 1.39 g of 2-[2-(1-benzofuran-5-yl)ethoxy]-1-(3-hydroxy-1-pyrrolidinyl)-1-ethanone, and 14.4 mL of a 1 mol/L solution of a borane-tetrahydrofuran complex in tetrahydrofuran was added dropwise thereto under ice-cooling, after which the resulting mixture was stirred at room temperature for 17 hours. To the reaction mixture was added 8.0 mL of 6 mol/L hydrochloric acid, and the resulting mixture was heated under reflux for 1 hour. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 10 with a 2 mol/L aqueous sodium hydroxide solution, and then the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 10:1) to obtain 0.96 g of 1-{2-[2-(1-benzofuran-5-yl)ethoxy]ethyl}-3-pyrrolidinol as a colorless oil.

Workup

  1. additionwas added dropwise
  2. temperatureunder ice-cooling
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for 1 hour
  5. temperatureAfter the reaction mixture was cooled
  6. customthe organic layer was separated
  7. washThe organic layer was washed with water
  8. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 10:1)

Sources & evidence

ORD record
ord-9e20bdbcf0c045068d1dcc92227c0905
Source dataset
uspto-grants-2012_03
Patent number
US08129535B2

Reaction notes

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