Ammonium formate → Gabapentin Enacarbil

HRID 30520

反応式

HRID 30520 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 9883933Gabapentin Enacarbil収率 78%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1570e925a91e42cf93bbf232624772ed
出典データセット
uspto-grants-2008_09
特許番号
US07423169B2

関連ノート

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