Hydrogen Peroxide → (S)-4-[(1R,2R)-2-tert-butyl-diphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-2-hydroxy-6-methylmorpholin-3-one

HRID 16333

Reaktionsgleichung

Reaktionsgleichung von HRID 16333
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[Si:15]([O:32][C@H:33]([CH3:53])[C@H:34]([N:44]1[CH2:49][C@H:48]([CH3:50])[O:47][C:46](=[O:51])[C:45]1=[O:52])[C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].OO.S([O-])(O)=O.[Na+]>C(OCC)(=O)C.C1COCC1>[Si:15]([O:32][C@H:33]([CH3:53])[C@H:34]([N:44]1[CH2:49][CH:48]([CH3:50])[O:47][C@H:46]([OH:51])[C:45]1=[O:52])[C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)([C:28]([CH3:29])([CH3:31])[CH3:30])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

8

Edukt 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 23665763Sodium BisulfiteHCID 68718625(S)-4-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-6-methylmorpholine-2,3-dione

Produkt 1

HCID 68717084(S)-4-[(1R,2R)-2-tert-butyl-diphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-2-hydroxy-6-methylmorpholin-3-oneAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

In nitrogen atmosphere, a THF solution (0.25 mL) of 1.06 M lithium tri-sec-butyl borohydride was dropwise added to a THF solution (3 mL) of (S)-4-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-6-methylmorpholin-2,3-dione (95 mg) at −20° C. This reaction solution was stirred at −20° C. for 30 min. To this reaction solution, a 5 N sodium hydroxide aqueous solution (0.03 mL) and a 30% hydrogen peroxide aqueous solution (0.07 mL) were added. This reaction solution was stirred under ice-cooling for 1 hr. A sodium hydrogensulfite powder (20 mg) was added to the reaction solution, and this reaction solution was stirred at room temperature for 30 min. To this reaction solution, saturated saline and ethyl acetate were added. The organic layer was separated, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent; heptane ethyl acetate=1:1) to give 93 mg of the title compound. The physical property values of this compound were as follows:

Aufarbeitung

  1. stirringThis reaction solution was stirred under ice-
  2. temperaturecooling for 1 hr
  3. stirringthis reaction solution was stirred at room temperature for 30 min
  4. customThe organic layer was separated
  5. washwashed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (eluting solvent; heptane ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-5751d1605b924848abd1cef897baba5b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737141B2

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