Sodium Chloride → 1-(4-Hydroxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylic acid

HRID 2225517

반응식

HRID 2225517 반응식
C([O-])=O.[NH4+].C([O:8][C:9]1[CH:31]=[CH:30][C:12]([CH:13]=[CH:14][C:15]([N:17]2[CH2:22][CH2:21][C:20]([CH3:29])([C:23]([O:25]CC=C)=[O:24])[CH2:19][CH2:18]2)=[O:16])=[CH:11][C:10]=1[O:32][CH3:33])C=C.[Cl-].[Na+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:8][C:9]1[CH:31]=[CH:30][C:12]([CH:13]=[CH:14][C:15]([N:17]2[CH2:22][CH2:21][C:20]([CH3:29])([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]2)=[O:16])=[CH:11][C:10]=1[O:32][CH3:33]

참가 물질

6

반응물 3

HCID 5234Sodium ChlorideHCID 2723923Ammonium formateHCID 53899198Allyl 1-(4-allyloxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylate

생성물 1

HCID 536577511-(4-Hydroxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylic acid수율 125.1%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

0.4 g of bis(triphenylphosphine)palladium dichloride and 5 g of ammonium formate were added to a solution of 1.1 g of allyl 1-(4-allyloxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylate (Example 67) in 100 ml of THF. Under an argon stream, the solution was reacted for hours, while it was refluxed. After reaction, 150 ml of an aqueous sodium chloride solution was added to the reaction solution. The solution was extracted three times with 50 ml of ethyl acetate. The organic layer obtained was washed three times with an aqueous sodium chloride solution and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo, yielding 1.1 g of 1-(4-hydroxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylic acid (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

후처리

  1. customUnder an argon stream, the solution was reacted for hours, while it
  2. temperaturewas refluxed
  3. additionwas added to the reaction solution
  4. extractionThe solution was extracted three times with 50 ml of ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed three times with an aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThereafter, the solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-e22296aa17354f3abaa1c0380a77b429
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05344845

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