Morpholine → Gabapentin Enacarbil

HRID 30519

反応式

HRID 30519 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].N1CCOCC1>C(#N)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[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 8083MorpholineHCID 9999163Allyl 1-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

生成物 1

HCID 9883933Gabapentin Enacarbil

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of compound (15) (1 g, 2.7 mmol) in acetonitrile (10 mL) under nitrogen was added (10 mg, 0.008 mmol) of tetrakis(triphenylphosphine) palladium (0) followed by morpholine (0.28 mL, 0.28 g, 3.2 mmol). After one hour, the solvent was removed in vacuo. The resulting oil was dissolved in diethyl ether (50 mL) and the organic phase was washed with 2N HCl (20 mL), water (20 mL) and brine (20 mL). The ether layer was dried over anhydrous sodium sulfate and concentrated to give an oil, which was purified by column chromatography on silica gel, eluting with 30% ethyl acetate:hexane. The desired product (11) was isolated as a white crystalline solid (0.75 g, 84% yield), m.p 63-64° C.

後処理

  1. customthe solvent was removed in vacuo
  2. dissolutionThe resulting oil was dissolved in diethyl ether (50 mL)
  3. washthe organic phase was washed with 2N HCl (20 mL), water (20 mL) and brine (20 mL)
  4. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give an oil, which
  7. customwas purified by column chromatography on silica gel
  8. washeluting with 30% ethyl acetate

出典と根拠

ORDレコード
ord-3f5fa7b35b8f40caab56e0df7f730e98
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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