Sodium Methoxide → 1,1,1-Trifluoro-2-(4-(4-(1-tosylpiperidin-4-yl)oxazol-5-yl)phenyl)propan-2-ol

HRID 1616344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616344
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[CH:4]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5]1)#[C-:2].C[O-].[Na+].[F:33][C:34]([F:47])([F:46])[C:35]([C:38]1[CH:45]=[CH:44][C:41]([CH:42]=[O:43])=[CH:40][CH:39]=1)([OH:37])[CH3:36]>CO.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[F:33][C:34]([F:46])([F:47])[C:35]([C:38]1[CH:45]=[CH:44][C:41]([C:42]2[O:43][CH:2]=[N:1][C:3]=2[CH:4]2[CH2:5][CH2:6][N:7]([S:10]([C:13]3[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=3)(=[O:11])=[O:12])[CH2:8][CH2:9]2)=[CH:40][CH:39]=1)([OH:37])[CH3:36]

Komponenten

7

Edukt 3

HCID 10942334Sodium MethoxideHCID 595655894-(Isocyano(tosyl)methyl)-1-tosylpiperidineHCID 595655994-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)benzaldehyde

Produkt 1

HCID 252039711,1,1-Trifluoro-2-(4-(4-(1-tosylpiperidin-4-yl)oxazol-5-yl)phenyl)propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-(Isocyano(tosyl)methyl)-1-tosylpiperidine (260 mg, 0.73 mmol) was dissolved in MeOH (6 mL) and treated with sodium methoxide (1.0 M solution in MeOH, 0.7 mL), and 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzaldehyde (159 mg, 0.73 mmol) was then added. After being stirred at 80° C. for 2 h, the mixture was then cooled to r.t. and diluted with ethyl acetate (80 mL) and saturated aqueous NaHCO3 (30 mL). The separated organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (15% EtOAc/hexane) to provide 1,1,1-trifluoro-2-(4-(4-(1-tosylpiperidin-4-yl)oxazol-5-yl)phenyl)propan-2-ol as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.83 (s, 1H), 7.69-7.65 (m, 2H), 7.51-7.49 (m, 2H), 7.36-7.33 (m, 4H), 3.90 (d, J=11.7 Hz, 2H), 3.30-3.28 (s, 1H), 2.79 (tt, J=3.9 Hz, 11.7 Hz, 1H), 2.45 (s, 3H), 2.37 (td, J=2.3 Hz, 12.1 Hz, 2H), 2.17-2.07 (m, 2H), 1.85 (d, J=12.1 Hz, 2H), 1.80 (s, 3H); MS (ESI) 495.1 (M+H)+.

Aufarbeitung

  1. additionwas then added
  2. temperaturethe mixture was then cooled to r.t.
  3. dry with materialThe separated organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (15% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-40687ac5d5604f9c9db46fb4ee435620
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765788B2

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