Hydrochloric Acid → (S)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride

HRID 751617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751617
C(OC(=O)[NH:7][C@@H:8]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.[ClH:27].O1CCOCC1>CO>[ClH:27].[NH2:7][C@@H:8]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[C:9]([N:11]1[CH2:12][CH2:13][CH:14]([OH:17])[CH2:15][CH2:16]1)=[O:10]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 10808894[(S)-1-(4-Fluoro-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 67278381(S)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Route A: To a solution of [1 (S)-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]carbamic acid tert-butyl ester (Preparation 19, 11.6 g, 31.7 mmol) in methanol (40 mL) was added hydrochloric acid in dioxane (24 mL, 4N, 95.0 mmol) and the reaction mixture stirred at rt for 6 h. The solvent was removed in vacuo and the residue was dissolved in water (100 mL) and extracted into ethyl acetate (2×50 mL). The aqueous phase was evaporated to dryness to give the title compound as a white solid. δH (D2O): 0.52–0.63 (0.5H, m), 1.12–1.23 (0.5H, m), 1.26–1.38 (1H, m), 1.42–1.50 (0.5H, m), 1.59–1.69 (0.5H, m), 1.72–1.82 (1H, m), 2.61–2.71 (0.5H, m), 2.91–3.15 (4H, m), 3.33–3.47 (1H, m), 3.69–3.78 (1H, m), 3.88–3.96 (1H, m), 4.60–4.72 (1H, m), 7.02–7.11 (2H, m), 7.14–7.26 (2H, m).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water (100 mL)
  3. extractionextracted into ethyl acetate (2×50 mL)
  4. customThe aqueous phase was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ae13250f2e7b44b4b50e3af7bbf64cf3
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405210B2

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