{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(1-methyl-1H-imidazol-5-yl)methanol → {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(1-methyl-1H-imidazol-5-yl)methanone

HRID 577858

Reaktionsgleichung

Reaktionsgleichung von HRID 577858
[Si:1]([O:18][CH2:19][C:20]1[C:21]([N:36]2[CH2:41][C@H:40]([CH3:42])[O:39][C@H:38]([CH3:43])[CH2:37]2)=[C:22]([F:35])[C:23]([F:34])=[C:24]([CH:26]([C:28]2[N:32]([CH3:33])[CH:31]=[N:30][CH:29]=2)[OH:27])[CH:25]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.O=[Mn]=O>[Si:1]([O:18][CH2:19][C:20]1[C:21]([N:36]2[CH2:37][C@H:38]([CH3:43])[O:39][C@H:40]([CH3:42])[CH2:41]2)=[C:22]([F:35])[C:23]([F:34])=[C:24]([C:26]([C:28]2[N:32]([CH3:33])[CH:31]=[N:30][CH:29]=2)=[O:27])[CH:25]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

4

Edukt 1

HCID 86658060{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(1-methyl-1H-imidazol-5-yl)methanol2×

Produkt 1

HCID 87369084{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(1-methyl-1H-imidazol-5-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the solution of {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(1-methyl-1H-imidazol-5-yl)methanol (Intermediate 69, 50 mg, 0.08 mmol) in anhydrous DCM (5 mL), MnO2 (143 mg, 1.65 mmol) was added at 0° C. and allowed to stir for 1 hour at room temperature. The reaction mixture was filtered and the solvents were removed under vacuum and the residue was purified over silica gel chromatography column using ethyl acetate-pet. ether gradient to give solid. Yield: 37 mg, (75%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe solvents were removed under vacuum
  3. customthe residue was purified over silica gel chromatography column
  4. customto give solid

Quellen und Nachweise

ORD-Eintrag
ord-a4ef54baf8c74f86a7bc1d77d8303361
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040528B2

Verknüpfte Notizen

Wird geladen…