Sodium Bicarbonate → (R)-2-methyl-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)propane-2-sulfinamide

HRID 715343

Reaktionsgleichung

Reaktionsgleichung von HRID 715343
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[N:10]=[CH:9][C:8]([C:11](=O)[CH3:12])=[CH:7][CH:6]=1.[CH3:16][C:17]([S@:20]([NH2:22])=[O:21])([CH3:19])[CH3:18].[BH4-].[Na+].C(=O)([O-])O.[Na+]>C1COCC1.CCO.CCO.CCO.CCO.[Ti]>[CH3:16][C:17]([S@:20]([NH:22][CH:11]([C:8]1[CH:9]=[N:10][C:5]([O:4][CH2:3][C:2]([F:15])([F:14])[F:1])=[CH:6][CH:7]=1)[CH3:12])=[O:21])([CH3:19])[CH3:18]

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 58629124Ethanone, 1-[6-(2,2,2-trifluoroethoxy)-3-pyridinyl]-

Produkt 1

HCID 67510902(R)-2-methyl-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)propane-2-sulfinamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724286Titanium(IV)ethoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanone (4.51 g, 20.58 mmol, Step-3), (R)-2-methylpropane-2-sulfinamide (3.74 g, 30.9 mmol) and tetraethyl orthotitanate (6.47 mL, 30.9 mmol) in THF (23 mL) is stirred at 70° C. for 17 hours. The reaction mixture is cooled to 0° C., sodium borohydride (2.72 g, 72.0 mmol) is added there, and the mixture is stirred at the same temperature for 1 hour. Saturated aqueous sodium hydrogen carbonate (50 mL) is added to the reaction mixture, and the mixture is stirred for 10 minutes. After filtration through a pad of Celite™, the filtrate is extracted with EtOAc (300 mL). The organic layer is washed with water (100 mL×2) and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (4:1 to 1:1) to give 6.25 g (94% yield) of the title compound as colorless oil.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. stirringthe mixture is stirred at the same temperature for 1 hour
  3. stirringthe mixture is stirred for 10 minutes
  4. filtrationAfter filtration through a pad of Celite™
  5. extractionthe filtrate is extracted with EtOAc (300 mL)
  6. washThe organic layer is washed with water (100 mL×2)
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate is concentrated in vacuo
  10. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (4:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8ac734a53f2547ec944670887b4578ac
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187475B2

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