Potassium tert-butoxide → 3-(5-Bromo-4-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

HRID 1022388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022388
CO[C:3]([C:5]1([NH:13][C:14](=[O:25])[CH2:15][C:16]2[CH:21]=[C:20]([Br:22])[C:19]([F:23])=[CH:18][C:17]=2[CH3:24])[CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]1)=[O:4].CC(C)([O-])C.[K+]>CN(C)C=O>[Br:22][C:20]1[C:19]([F:23])=[CH:18][C:17]([CH3:24])=[C:16]([C:15]2[C:14](=[O:25])[NH:13][C:5]3([CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]3)[C:3]=2[OH:4])[CH:21]=1

Komponenten

4

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 596145984-[2-(5-Bromo-4-fluoro-2-methyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester

Produkt 1

HCID 596145973-(5-Bromo-4-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(5-bromo-4-fluoro-2-methyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester (6.0 g) in dimethylformamide (20 ml) at 100° C. is added potassium tert-butoxide (3.23 g) and stirring continued at 100° C. for 10 minutes. The reaction mixture is quenched at room temperature by addition of acetic acid (1.64 ml), diluted with water (20 ml) and extracted with tert-butyl methyl ether (3×). The combined organic layers are washed with brine, dried over sodium sulfate and concentrated. The residue is triturated with acetonitrile, filtered and dried. Yield: 3.69 g of 3-(5-bromo-4-fluoro-2-methyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one as a solid, mp: 229-230° C.

Aufarbeitung

  1. customThe reaction mixture is quenched at room temperature by addition of acetic acid (1.64 ml)
  2. additiondiluted with water (20 ml)
  3. extractionextracted with tert-butyl methyl ether (3×)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is triturated with acetonitrile
  8. filtrationfiltered
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0f8ae5b9e44a4ed380eb39dbf4be8a53
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722578B2

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