Potassium Hydroxide → 1-(1-((tert-butoxy)carbonyl)piperidin-4-yl)-1H-pyrazole-4-carboxylic acid

HRID 1427010

Reaktionsgleichung

Reaktionsgleichung von HRID 1427010
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[CH:10]=1)=[O:5])C.[OH-].[K+]>CO.O>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 45926154Tert-butyl 4-(4-(ethoxycarbonyl)-1H-pyrazol-1-YL)piperidine-1-carboxylate

Produkt 1

HCID 534858971-(1-((tert-butoxy)carbonyl)piperidin-4-yl)-1H-pyrazole-4-carboxylic acidAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

tert-Butyl 4-(4-(ethoxycarbonyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate described in Production Example 13-2 (2.11 g, 6.53 mmol) was dissolved in methanol (60 mL), then potassium hydroxide (1.46 g, 26.1 mmol) dissolved in water (16 mL) was added, and then the mixture was stirred for 27 hours. The reaction mixture was concentrated under vacuum and diethyl ether was added for partition. Ethyl acetate was added to the aqueous layer for dilution, then a 5% aqueous potassium hydrogensulfate solution was added for acidification, and the mixture was extracted with ethyl acetate twice. The combined organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated to obtain the title compound (1.58 g, 82%).

Aufarbeitung

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under vacuum and diethyl ether
  3. additionwas added
  4. customfor partition
  5. additionEthyl acetate was added to the aqueous layer for dilution
  6. additiona 5% aqueous potassium hydrogensulfate solution was added for acidification
  7. extractionthe mixture was extracted with ethyl acetate twice
  8. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-883a07d1c3fe4d91b9caad0dafa139ef
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933099B2

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