Lithium hydroxide, monohydrate → HCID 71226525, Verbindung

HRID 713449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 713449
C([O:3][C:4](=[O:24])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH2:8][CH2:7]1)C.O[Li].O>>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[O:19][CH3:20])[C:12]([CH:9]1[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:24])=[O:3])[CH2:11][CH2:10]1)=[O:23]

Komponenten

3

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 71226849[4-(3,4-Dimethoxy-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester

Produkt 1

HCID 71226525HCID 71226525, VerbindungAusbeute 92,5 %

Versuchsvorschrift

To a solution of [4-(3,4-dimethoxy-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester (0.45 g, 1.34 mmol in 6 mL of THF and 2 mL of methanol) was added LiOH.H2O (0.28 g, 6.7 mmol in 3 mL of water) and the reaction mixture was stirred at ambient temperature for 1.5 hours. The solvent was removed in vacuo then diluted with 20 mL of water (pH 14). The residue was treated with 12 mL of 1 N HCl (pH 4), frozen at −78° C. and lyophilized for 24 hours to yield the title compound (0.40 g, 1.24 mmol). MS (ESI) m/z 308.3 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.16 min.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. additionthen diluted with 20 mL of water (pH 14)
  3. additionThe residue was treated with 12 mL of 1 N HCl (pH 4)
  4. temperaturefrozen at −78° C.
  5. waitlyophilized for 24 hours

Quellen und Nachweise

ORD-Eintrag
ord-be4eb5b839184aa59b71d2b78d54024a
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181266B2

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