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Methyl morpholine oxide → 3-bromo-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methyl-5-(trifluoromethyl)benzamide

HRID 426082
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 426082
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[C:5]([N:7]([CH2:9][C@H:10]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:11][CH:12]=C)[CH3:8])=[O:6].C[N+]1([O-])CC[O:32]CC1.OS([O-])=O.[Na+]>CC(C)=O.O.O=[Os](=O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[C:5]([N:7]([CH2:9][C@H:10]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:11][CH:12]=[O:32])[CH3:8])=[O:6]
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Komponenten

7

Edukt 3

HCID 82029Methyl morpholine oxideHCID 161193783-bromo-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-5-(trifluoromethyl)benzamideHCID 23665763Sodium Bisulfite

Produkt 1

HCID 159506583-bromo-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methyl-5-(trifluoromethyl)benzamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318
Osmium Tetroxide
Katalysator
HCID 180AcetoneLösungsmittel
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of 3-bromo-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-5-(trifluoromethyl)benzamide (0.86 g, 1.9 mmol) in acetone (45 mL) were added OsO4 (2.5% in t-butyl alcohol, 0.49 mL, 0.039 mmol) and 4-methylmorpholine-4-oxide (0.41 g, 3.5 mmol). The solution was stirred under nitrogen at RT overnight and then an aqueous solution of NaHSO3 (39%, 45 mL) was added. The mixture was stirred for 2 h, diluted with water and then extracted twice with methylene chloride. The combined organic solutions were separated by means of a phase separator column and the solvent was removed by evaporation. The residue (1.08 g) was dissolved in THF (18 mL) and water (4.5 mL) and to the resultant solution was added NaIO4 (0.73 g, 3.4 mmol). The mixture was stirred under nitrogen overnight at RT. The mixture was partitioned between methylene chloride and water. The aqueous phase was extracted with methylene chloride and then the combined organic solutions were washed with brine and separated by means of a phase separator column. The solvent was removed by evaporation. There was obtained 0.78 g (90%) of the title compound. 1H NMR (500 MHz, CDCl3): 2.4-4.4 (cm, 8H), 6.2-8.2 (cm, 7H), 9.8 (s, 1H); LCMS: m/z 447 (M+1)+.

Aufarbeitung

  1. stirringThe mixture was stirred for 2 h
  2. extractionextracted twice with methylene chloride
  3. customThe combined organic solutions were separated by means of a phase separator column
  4. customthe solvent was removed by evaporation
  5. dissolutionThe residue (1.08 g) was dissolved in THF (18 mL)
  6. stirringThe mixture was stirred under nitrogen overnight at RT
  7. customThe mixture was partitioned between methylene chloride and water
  8. extractionThe aqueous phase was extracted with methylene chloride
  9. washthe combined organic solutions were washed with brine
  10. customseparated by means of a phase separator column
  11. customThe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-41de88ab68784e74bba23a8ef9cea7ab
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08106208B2

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