Acetonitrile → 3-(3-Chloro-5-fluorophenyl)-1-propylpyrrolidin-3-ol

HRID 1931812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1931812
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(#N)C.C(=O)([O-])[O-].[K+].[K+].I[CH2:25][CH2:26][CH3:27]>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH2:25][CH2:26][CH3:27])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 685156533-(3-Chloro-5-fluorophenyl)pyrrolidin-3-ol

Produkt 1

HCID 251438103-(3-Chloro-5-fluorophenyl)-1-propylpyrrolidin-3-olAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-(3-chloro-5-fluorophenyl)pyrrolidin-3-ol (1.10 g, 5 mmol), acetonitrile (20 mL), potassium carbonate (1.4 g, 10.1 mmol) and iodopropane (1.13 mg, 6.65 mmol) was stirred at ambient temperature for 2 h. The temperature was shortly raised to 40° C. twice during this period. Water was added and the aqueous phase was extracted with ethyl acetate, the combined organic phase was dried (MgSO4), and evaporated. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1) gave the title compound (0.57 g). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diisopropyl ether: M.p. 157.2° C.; MS m/z (relative intensity, 70 eV) 257 (M+, 8), 228 (bp), 198 (46), 129 (36), 84 (59).

Aufarbeitung

  1. temperatureThe temperature was shortly raised to 40° C. twice during this period
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. customevaporated
  5. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3b915811153f41f783d92f9b10cadc26
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188301B2

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