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Sodium Sulfate → 2-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]ethanol

HRID 1436115
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1436115
[BH4-].[Li+].[Si:3]([O:20][C@H:21]([CH3:39])[C@H:22]([NH:32][CH2:33][C:34](OCC)=[O:35])[C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[C:25]([F:31])[CH:24]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Si:3]([O:20][C@H:21]([CH3:39])[C@H:22]([NH:32][CH2:33][CH2:34][OH:35])[C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[C:25]([F:31])[CH:24]=1)([C:16]([CH3:18])([CH3:19])[CH3:17])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
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Komponenten

5

Edukt 3

HCID 24436Sodium SulfateHCID 4148881Lithium borohydrideHCID 86633283ethyl [(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]acetate

Produkt 1

HCID 689073882-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]ethanolAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Lithium borohydride (20 mg) was added to a solution of ethyl [(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]acetate (158 mg) in THF (3 ml) in a nitrogen atmosphere, and the reaction solution was stirred at room temperature for one day. A saturated sodium sulfate solution was added to the reaction solution, and then the precipitated insoluble matter was removed by filtration through celite. Methanol was added to the filtrate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain 103 mg of the title compound.

Aufarbeitung

  1. customthe precipitated insoluble matter was removed by filtration through celite
  2. additionMethanol was added to the filtrate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-7092199bd42b43baba168944743a1fb7
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07618960B2

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