Reaktion #684996

Reaktionsgleichung

water

acetone

2-(2-(1-benzothiophene-6-yl)ethoxy)-1-(3-hydroxy-1-pyrrolidinyl)-1-ethanone

hydrochloric acid

→

yellow oil

1-(2-(2-(1-benzothiophene-6-yl)ethoxy)ethyl)-3-pyrrolidinol

Lösungsmittel

tetrahydrofuran

ethyl acetate

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise to the obtained solution
2. 2
   Temperaturwhile cooling on ice
3. 3
   workup.STIRRINGthe obtained mixture was then stirred for 30 minutes
4. 4
   Temperaturthe obtained mixture was heated
5. 5
   Temperaturto reflux for 2 hours
6. 6
   TemperaturAfter the reaction mixture was cooled
7. 7
   Sonstigea water layer was separated
8. 8
   workup.ADDITIONThereafter, ethyl acetate was added to the water layer
9. 9
   workup.ADDITIONThe pH of the obtained mixture was adjusted to pH 9.5 by addition of a 2 mol/l aqueous sodium hydroxide solution
10. 10
    Sonstigefollowed by separation of an organic layer
11. 11
    WaschenThe organic layer was successively washed with water
12. 12
    Trocknena saturated saline solution, and then dried over anhydrous magnesium sulfate
13. 13
    workup.DISTILLATIONThereafter, the solvent was distilled away under a reduced pressure
14. 14
    SonstigeThe residue was purified by column chromatography (eluent; chloroform:methanol=30:1 to 20:1)

Vorschrift

The above 2-(2-(1-benzothiophene-6-yl)ethoxy)-1-(3-hydroxy-1-pyrrolidinyl)-1-ethanone was dissolved in 7.4 ml of tetrahydrofuran. Thereafter, 7.4 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, 10 ml of acetone was added to the reaction mixture, and the obtained mixture was then stirred for 30 minutes. Thereafter, 1.5 ml of 6 mol/l hydrochloric acid was added thereto, and the obtained mixture was heated to reflux for 2 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto, and a water layer was separated. Thereafter, ethyl acetate was added to the water layer. The pH of the obtained mixture was adjusted to pH 9.5 by addition of a 2 mol/l aqueous sodium hydroxide solution, followed by separation of an organic layer. 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 20:1), so as to obtain 0.53 g of a yellow oil product, 1-(2-(2-(1-benzothiophene-6-yl)ethoxy)ethyl)-3-pyrrolidinol.

Quelle