1-(4-[(Allyloxy)carbonyl]phenyl)piperidine-4-carboxylic acid ethyl ester → 4-[4-(Ethoxycarbonyl)piperidin-1-YL]benzoic acid

HRID 2196490ノート

反応式

HRID 2196490 の反応式
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20]CC=C)=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C1COCC1.N1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([OH:20])=[O:19])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

参加物

5

反応物 1

HCID 579867021-(4-[(Allyloxy)carbonyl]phenyl)piperidine-4-carboxylic acid ethyl ester

生成物 1

HCID 190638644-[4-(Ethoxycarbonyl)piperidin-1-YL]benzoic acid収率 65.9%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8083Morpholine溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4.74 g of 1-{4-[(allyloxy)carbonyl]phenyl}piperidine-4-carboxylic acid ethyl ester in 75 ml of THF, 2.10 ml of morpholine and 390 mg of tetrakis(triphenylphosphine)palladium were added, and the mixture was stirred at 60° C. for 1.5 hours. After the solvent was evaporated under reduced pressure, EtOAc was added to the residue, and the reaction solution was washed with NaHCO3 aq. three times. To the collected saturated NaHCO3 aq., conc. HCl was added, and the produced precipitate was collected by filtration and dried under reduced pressure to obtain 2.73 g of 4-[4-(Ethoxycarbonyl)piperidin-1-yl]benzoic acid.

後処理

  1. customAfter the solvent was evaporated under reduced pressure, EtOAc
  2. additionwas added to the residue
  3. washthe reaction solution was washed with NaHCO3 aq. three times
  4. additionTo the collected saturated NaHCO3 aq., conc. HCl was added
  5. filtrationthe produced precipitate was collected by filtration
  6. customdried under reduced pressure

出典と根拠

ORDレコード
ord-272c776520d84a2397fe7eee6d517a18
出典データセット
uspto-grants-2012_12
特許番号
US08338429B2

反応ノート

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