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

HRID 2225517

反応式

HRID 2225517 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-e22296aa17354f3abaa1c0380a77b429
出典データセット
uspto-grants-1994_09
特許番号
US05344845

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