Ammonium formate → Gabapentin Enacarbil

HRID 30518

반응식

HRID 30518 반응식
C([O-])=O.[NH4+].[C:5]([O:10][CH:11]([O:13][C:14]([NH:16][CH2:17][C:18]1([CH2:24][C:25]([O:27]CC=C)=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:15])[CH3:12])(=[O:9])[CH:6]([CH3:8])[CH3:7]>C(O)C.[Pd]>[C:5]([O:10][CH:11]([O:13][C:14]([NH:16][CH2:17][C:18]1([CH2:24][C:25]([OH:27])=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:15])[CH3:12])(=[O:9])[CH:6]([CH3:8])[CH3:7]

참가 물질

5

반응물 2

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

생성물 1

HCID 9883933Gabapentin Enacarbil

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a stirred suspension of ammonium formate (3.4 g, 54 mmol) in ethanol (34 mL), was added compound (15) (10 g, 27 mmol) together with 10% Pd/C (1 g) under a nitrogen atmosphere. After one hour, the reaction mixture was filtered and the catalyst washed with ethanol (2×10 mL). The filtrates were combined and evaporated. The crude product was dissolved in diethyl ether (150 mL) and the organic phase was washed with 2N HCl (100 mL), water (100 mL) and brine (100 mL). The ether layer was dried over anhydrous sodium sulfate and concentrated to give a viscous liquid that crystallized upon standing. The product was recrystallized using 1:10 ethyl acetate:heptane (100 mL) to give the product (11) as a white, crystalline solid (7.9 g, 88%), m.p 63-64° C.

후처리

  1. filtrationthe reaction mixture was filtered
  2. washthe catalyst washed with ethanol (2×10 mL)
  3. customevaporated
  4. dissolutionThe crude product was dissolved in diethyl ether (150 mL)
  5. washthe organic phase was washed with 2N HCl (100 mL), water (100 mL) and brine (100 mL)
  6. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto give a viscous liquid that
  9. customcrystallized
  10. customThe product was recrystallized

출처 및 근거

ORD 기록
ord-191ae72a0ffa4cf7a192af7f165a1881
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423169B2

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