Iodoethane → 3-(3,4-Difluorophenyl)-1-ethyl-3-methoxypyrrolidine

HRID 1188155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188155
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].I[CH2:23][CH3:24].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][N:11]([CH2:23][CH3:24])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

7

Edukt 4

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 462192213-(3,4-Difluorophenyl)-3-methoxypyrrolidine

Produkt 1

HCID 462192223-(3,4-Difluorophenyl)-1-ethyl-3-methoxypyrrolidineAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-(3,4-difluorophenyl)-3-methoxypyrrolidine (0.19 g, 0.89 mmol) in acetonitrile (5 ml), potassium carbonate (0.17 g, 1.25 mmol) and iodoethane (0.075 ml, 0.94 mmol) was added and the mixture was stirred at ambient temperature for 5 h. Aqueous sodiumcarbonate (10%, 50 ml) and ethyl acetate (50 ml) was added and the organic phase was collected. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phase was washed with Brine, dried (Na2SO4) and evaporated to give the crude product. Purification on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) followed by flash column chromatography on silica gel (EtOAc/MeOH 4:1) gave the title compound (0.10 g, 46%). The amine was converted to the oxalic acid salt and recrystallized from methanol/diethyl ether: M.p. 135-136° C. MS m/z (rel. intensity, 70 eV) 241 (4), 226 (27), 211(17), 141 (26), 71 (bp).

Aufarbeitung

  1. customthe organic phase was collected
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  3. washthe combined organic phase was washed with Brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give the crude product
  7. customPurification
  8. washon a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-5c34c117cc944187a3aab3075310f21e
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673962B2

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