Morpholine → Gabapentin Enacarbil

HRID 1767290

반응식

HRID 1767290 반응식
[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]

참가 물질

5

반응물 2

HCID 8083MorpholineHCID 9999163Allyl 1-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

생성물 1

HCID 9883933Gabapentin Enacarbil

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-67c2575901d44143b82ddf25c02faef2
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07232924B2

연결된 노트

불러오는 중…