Diethyl Ether → (S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol

HRID 16331

Reaktionsgleichung

Reaktionsgleichung von HRID 16331
C(OCC)C.[CH2:6]1[O:9][C@H:7]1[CH3:8].[Si:10]([O:27][C@H:28]([CH3:40])[C@H:29]([NH2:39])[C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl([O-])(=O)(=O)=O.[Li+]>O.C(Cl)Cl>[Si:10]([O:27][C@H:28]([CH3:40])[C@H:29]([NH:39][CH2:6][C@@H:7]([OH:9])[CH3:8])[C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=1)([C:23]([CH3:24])([CH3:25])[CH3:26])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

7

Edukt 4

HCID 3283Diethyl Ether2×HCID 146262(2S)-2-MethyloxiraneHCID 23665649Lithium perchlorateHCID 68719033(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine

Produkt 1

HCID 68718733(S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A diethyl ether solution (1 mL) of (S)-(−)-propylene oxide (0.1 mL) and (1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine (212 mg) was added to a diethyl ether suspension (1 mL) of lithium perchlorate (750 mg). This reaction solution was stirred in nitrogen atmosphere at room temperature overnight. To this reaction solution, methylene chloride and iced-water were added. The organic layer was separated, and the water was re-extracted with methylene chloride. The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent; ethyl acetate:heptane=9:1 to 4:1) to give 172 mg of the title compound. The physical property values of this compound were as follows:

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe water was re-extracted with methylene chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluting solvent; ethyl acetate:heptane=9:1 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-22c09812ab944d188fe4d4c249879f9f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737141B2

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