Lithium hydroxide, monohydrate → (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid

HRID 59887

Reaktionsgleichung

Reaktionsgleichung von HRID 59887
[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19]([O:21]CC)=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2].O[Li].O>C1COCC1.O>[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2]

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 131737069ethyl (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylate

Produkt 1

HCID 118366221(R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acidAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

To a solution of ethyl (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylate (71.5 g, 193 mmol) in THF/H2O (1:1, 2 L) was added LiOH.H2O (24.2 g, 578 mmol) at 20-25° C. The reaction mixture was stirred at 20-25° C. for 24 hours. The mixture was concentrated, and the aqueous phase was washed with diethyl ether (2 times with 500 mL). The aqueous phase was acidified to pH 2 with 1N HCl (˜400 mL). The precipitated solid was filtered and dried to afford (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid (52 g, 78%). MS (ES+) 344.18 (M+H).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. washthe aqueous phase was washed with diethyl ether (2 times with 500 mL)
  3. filtrationThe precipitated solid was filtered
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7920f8588bf448158309a362e6ad18eb
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440949B2

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