Imidazole → tert-butyl [(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamate

HRID 1436109

Reaktionsgleichung

Reaktionsgleichung von HRID 1436109
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH:19][C@H:20]([CH3:39])[C@H:21]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[C:24]([F:30])[CH:23]=1.N1C=CN=C1.C(OCC)(=O)C>CN(C=O)C>[Si:5]([O:19][C@H:20]([CH3:39])[C@H:21]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[C:24]([F:30])[CH:23]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 94078tert-ButyldiphenylchlorosilaneHCID 68717986tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate

Produkt 1

HCID 68718850tert-butyl [(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Tert-Butylchlorodiphenylsilane (2.0 ml) was added in four portions to a solution of tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate (610 mg) and imidazole (817 mg) in DMF (3 ml) in a nitrogen atmosphere, and the reaction solution was stirred at room temperature for three hours. Ethyl acetate was added to the reaction solution, which was then sequentially washed with water, 1 N hydrochloric acid, water, a saturated sodium bicarbonate solution, and brine. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:diethyl ether 49:1 to 19:1) to obtain 684 mg of the title compound.

Aufarbeitung

  1. washwas then sequentially washed with water, 1 N hydrochloric acid, water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:diethyl ether 49:1 to 19:1)

Quellen und Nachweise

ORD-Eintrag
ord-9957fb2db56244fd8e50c55f3e00daa4
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618960B2

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