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Sodium Iodide → (R)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine

HRID 1859449
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1859449
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[OH:31][C@@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1>C(#N)C>[CH3:15][N:13]([CH3:14])[C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][N:34]2[CH2:35][CH2:36][C@@H:32]([OH:31])[CH2:33]2)=[CH:12][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2759337(R)-3-PyrrolidinolHCID 185347644-Dimethylaminophenethyl tosylate

Produkt 1

HCID 69902796(R)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

4-Dimethylaminophenethyl tosylate (1.91 g, 6.0 mmol), sodium carbonate (750 mg, 7.0 mmol) and sodium iodide (40 mg, 0.26 mmol) were added to a solution of (R)-3-hydroxypyrrolidine (522 mg, 6.0 mmol) in acetonitrile (40 ml), and they were heated under reflux at 90° C. for 4 hours. The solvent was evaporated under reduced pressure. The obtained residue was distributed in 2 M NaOH and chloroform. The organic layer was dried and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane, then with dichloromethane and methanol (50:1) and finally with a mixture of the same solvents (20:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (R)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine in the form of a light yellow oil (1.00 g, 71%).

Aufarbeitung

  1. temperaturewere heated
  2. customThe solvent was evaporated under reduced pressure
  3. customThe organic layer was dried
  4. customthe solvent was evaporated under reduced pressure
  5. washThe product was eluted with dichloromethane
  6. additionwith dichloromethane and methanol (50:1) and finally with a mixture of the same solvents (20:1)
  7. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d32f0010ef0e40e5a2bfeb0acd9db396
Quelldatensatz
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06528504B2

Notizen zur Reaktion

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