Sodium Hydroxide → 2-Cyclopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid

HRID 1753907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753907
C([O:3][C:4]([C:6]1[C:7]([CH:19]2[CH2:21][CH2:20]2)=[N:8][C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:10][C:11]=1[CH3:12])=[O:5])C.[OH-].[Na+]>CO.O1CCCC1>[CH:19]1([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[C:11]([CH3:12])[CH:10]=[C:9]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[N:8]=2)[CH2:21][CH2:20]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 708168332-Cyclopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid ethyl ester

Produkt 1

HCID 672877532-Cyclopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acidAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-cyclopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid ethyl ester (16.8 g, 57.8 mmol) in methanol-tetrahydrofuran (1:1) (90 ml) is treated for 3 days with a 2M aqueous solution of sodium hydroxide at reflux. The organic solvent is distilled off and the aqueous layer treated with 2M hydrochloric acid, and extracted with ethyl acetate. The combined organic layers are dried over magnesium sulphate and evaporated to dryness. The crude product is purified by flash chromatography (silica gel, 75% ethyl acetate/cyclohexane) to yield 2-cyclopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid (10.4 g, 39.6 mmol, 69%).

Aufarbeitung

  1. temperatureat reflux
  2. distillationThe organic solvent is distilled off
  3. additionthe aqueous layer treated with 2M hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers are dried over magnesium sulphate
  6. customevaporated to dryness
  7. customThe crude product is purified by flash chromatography (silica gel, 75% ethyl acetate/cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-318233f52fa744ad9a6e85af129487bd
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09168259B2

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