Trifluoroacetic acid → 4-(4-Fluorophenyl)-2,8-diazaspiro[4.5]decan-1-one

HRID 347307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347307
C(OC([N:8]1[CH2:25][CH2:24][C:11]2([C:15](=[O:16])[NH:14][CH2:13][CH:12]2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH:12]2[C:11]3([CH2:10][CH2:9][NH:8][CH2:25][CH2:24]3)[C:15](=[O:16])[NH:14][CH2:13]2)=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 115303634-(4-Fluoro-phenyl)-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester

Produkt 1

HCID 116391194-(4-Fluorophenyl)-2,8-diazaspiro[4.5]decan-1-oneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 4-(4-fluoro-phenyl)-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (46.0 g, 132 mmol) in DCM (260 mL) containing TFA (150 mL, 1.32 mol) was stirred vigorously at 0° C. for 15 min. The reaction mixture was then poured into NaOH (3 N, 200 mL) and the product extracted with DCM (3×100 mL). The combined organic extracts were then washed with water (100 mL) and brine (100 mL) and then dried over sodium sulfate. Filtration and evaporation afforded the title compound (22.14 g, 68%) as a white solid after trituration from ethyl acetate. MS: m/e=249.2 (M+H).

Aufarbeitung

  1. extractionthe product extracted with DCM (3×100 mL)
  2. washThe combined organic extracts were then washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-a4a8b216717c4c10af17803d57ee0104
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173133B2

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