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

HRID 16358

Reaktionsgleichung

Reaktionsgleichung von HRID 16358
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). The resulting reaction solution was stirred at room temperature for 11 hr, and a saturated sodium hydrogencarbonate aqueous solution and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated sodium hydrogencarbonate aqueous solution and with saturated saline in this order, and 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 resulting reaction solution
  2. customThe organic layer was separated
  3. washwashed with a saturated sodium hydrogencarbonate aqueous solution and with saturated saline in this order
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d1b2a85d4dcb4ddd8eee5a9a2e019bbc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737141B2

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