Lithium Hydroxide → 4-((1-(Tert-butoxycarbonyl)piperidin-4-YL)oxy)-2-methoxybenzoic acid

HRID 128582노트

반응식

HRID 128582 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Li+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

참가 물질

4

반응물 2

HCID 3939Lithium Hydroxide2회HCID 10570851Tert-butyl 4-(3-methoxy-4-(methoxycarbonyl)phenoxy)piperidine-1-carboxylate

생성물 1

HCID 105458744-((1-(Tert-butoxycarbonyl)piperidin-4-YL)oxy)-2-methoxybenzoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 2-methoxy-4-(1-Boc-4-piperidyloxy)benzoate (4.5 g, 12.3 mmol) was dissolved in THF (200 ml) and treated with a solution of lithium hydroxide (17 ml of a 1.1M aqueous solution, 18.7 mmol) added over 5 min. The mixture was stirred at ambient temperature for 72 hours. An additional 4 ml of 1.1M lithium hydroxide was added and the mixture was heated at reflux for 13 hours, then stirred at ambient temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo to give 2-methoxy-4-(1-Boc-4-piperidyloxy)benzoic acid.

후처리

  1. additionadded over 5 min
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 13 hours
  4. stirringstirred at ambient temperature for 18 hours
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. customthe residue partitioned between ethyl acetate and 1N hydrochloric acid
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness in vacuo

출처 및 근거

ORD 기록
ord-36d50e3a34ab4a4c942082d14fad05f0
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464788

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