Lithium Hydroxide → 2-(4-(1-(Tert-butoxycarbonyl)piperidin-4-yloxy)-2-methoxyphenyl)acetic acid

HRID 1292348

Reaktionsgleichung

Reaktionsgleichung von HRID 1292348
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:23][C:24]([O:26]C)=[O:25].[OH-].[Li+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:14][CH2:15]2)[CH:6]=[CH:5][C:4]=1[CH2:23][C:24]([OH:26])=[O:25]

Komponenten

4

Versuchsvorschrift

Methyl 2-methoxy-4-(1-Boc-4-piperidyloxy)phenylacetate (1.37 g, 3.6 mmol) was dissolved in THF (27 ml) and treated with lithium hydroxide (4.5 ml of a 1M aqueous solution, 4.5 mmol). The mixture was stirred at ambient temperature for 4.5 hours, then treated with an additional 0.9 ml of 1M lithium hydroxide and stirred at ambient temperature for 18 hours. The mixture was concentrated in vacuo, and the residue was acidified with 1M HCl, and extracted with ethyl acetate. The combined ethyl acetate layers were dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was reconcentrated from ether to give 2-methoxy-4-(1-Boc-4-piperidyloxy)phenylacetic acid.

Aufarbeitung

  1. stirringstirred at ambient temperature for 18 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f18b6242e2da413b9f697b4d24450bb6
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05756504

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