Dichloromethane → (1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine

HRID 16330

Reaktionsgleichung

Reaktionsgleichung von HRID 16330
FC(F)(F)C(O)=O.C(Cl)Cl.C(OC(=O)[NH:17][C@H:18]([C:39]1[CH:44]=[C:43]([F:45])[C:42]([F:46])=[C:41]([F:47])[CH:40]=1)[C@H:19]([O:21][Si:22]([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:20])(C)(C)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Si:22]([O:21][C@H:19]([CH3:20])[C@H:18]([NH2:17])[C:39]1[CH:44]=[C:43]([F:45])[C:42]([F:46])=[C:41]([F:47])[CH:40]=1)([C:35]([CH3:36])([CH3:37])[CH3:38])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68718850tert-butyl [(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamate

Produkt 1

HCID 68719033(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamineAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (0.5 mL) was added to a methylene chloride solution (2 mL) of [(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]carbamic acid tert-butyl ester (370 mg). This reaction solution was stirred at room temperature for 11 hr. To this reaction solution, a saturated sodium hydrogencarbonate aqueous solution and ethyl acetate were added. The organic layer was separated, washed with a saturated sodium hydrogencarbonate aqueous solution and then with saturated saline. Then, the organic layer was concentrated under reduced pressure to give 275 mg of the title compound. The physical property values of this compound were as follows:

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with a saturated sodium hydrogencarbonate aqueous solution
  3. concentrationThen, the organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e6ceb06e3c3d40b6964115651d1afece
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737141B2

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