Ammonium formate → Gabapentin Enacarbil

HRID 1767291

Reaktionsgleichung

Reaktionsgleichung von HRID 1767291
[C:1]([O:6][CH:7]([O:9][C:10]([NH:12][CH2:13][C:14]1([CH2:20][C:21]([O:23]CC=C)=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:11])[CH3:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].C([O-])=O.[NH4+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:6][CH:7]([O:9][C:10]([NH:12][CH2:13][C:14]1([CH2:20][C:21]([OH:23])=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:11])[CH3:8])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 9999163Allyl 1-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

Produkt 1

HCID 9883933Gabapentin EnacarbilAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of compound (15) (1 g, 2.7 mmol) in dioxane (9 mL) was added ammonium formate (341 mg, 2.7 mmol) and palladium (II) acetate (12 mg) under a nitrogen atmosphere. The reaction mixture was heated to reflux for one hour and then concentrated in vacuo. The resulting oily residue was taken up in diethyl ether (50 mL), washed with 2N HCl (20 mL), water (20 mL) and brine (20 mL). The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness. The crude compound was purified by column chromatography on silica gel, eluting with 30% ethyl acetate:hexane to give the desired product (11) as a colorless oil, which solidified on further standing at room temperature for 12 h (0.70 g, 78% yield), m.p. 62–64° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for one hour
  3. concentrationconcentrated in vacuo
  4. washwashed with 2N HCl (20 mL), water (20 mL) and brine (20 mL)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe crude compound was purified by column chromatography on silica gel
  8. washeluting with 30% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f12578b7709348e5b30d8001d0f8db5e
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07232924B2

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