Iodoethane → 3-(3-Chloro-2-fluorophenyl)-1-ethylpyrrolidin-3-ol

HRID 1931810

Reaktionsgleichung

Reaktionsgleichung von HRID 1931810
[Cl:1][C:2]1[C:3]([F:14])=[C:4]([C:8]2([OH:13])[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH3:23].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[C:3]([F:14])=[C:4]([C:8]2([OH:13])[CH2:12][CH2:11][N:10]([CH2:22][CH3:23])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 685157443-(3-Chloro-2-fluorophenyl)pyrrolidin-3-ol

Produkt 1

HCID 251436703-(3-Chloro-2-fluorophenyl)-1-ethylpyrrolidin-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a sealed tube a mixture of 3-(3-chloro-2-fluorophenyl)pyrrolidin-3-ol (0.5 g, 2.32 mmol), acetonitrile (3 mL), potassium carbonate (0.48 g, 3.48 mmol) and iodoethane (0.36 g, 2.32 mmol) was heated under microwave irradiation at 120° C. for 20 minutes. Aqueous sodium carbonate (10%, 50 mL) was added and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic phase was dried (Na2SO4) and evaporated. Purification by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 50:50) gave the title compound. The amine was converted to the fumaric acid salt and recrystallized from methanol/diethyl ether/diisopropyl ether (0.249 g). M.p. 142-145.5° C.; MS m/z (relative intensity, 70 eV) 243 (M+, 24), 228 (19), 157 (15), 72 (27), 71 (bp).

Aufarbeitung

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic phase was dried (Na2SO4)
  3. customevaporated
  4. customPurification by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-28bc2775f5854e0bbe554760e6ed6712
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188301B2

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