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

HRID 1615890노트

반응식

HRID 1615890 반응식
[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]

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8083Morpholine용매

실험 절차

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 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.

후처리

  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

출처 및 근거

ORD 기록
ord-562fd743fbe44d0d81ac1934754fdeaa
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765764B2

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