Water → N-(5'-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

HRID 1468074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468074
[F:1][C:2]1([F:25])[CH2:5][CH:4]([CH2:6][O:7][C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][C:13]4([CH2:22][CH2:21][CH:20]([O:23][CH3:24])[CH2:19][CH2:18]4)[C:14]3=O)=[CH:10][CH:9]=2)[CH2:3]1.[CH3:26][C:27]([S:30]([NH2:32])=[O:31])([CH3:29])[CH3:28].O>C(OCC)(=O)C.C(O[Ti](OCC)(OCC)OCC)C>[F:25][C:2]1([F:1])[CH2:5][CH:4]([CH2:6][O:7][C:8]2[CH:16]=[C:15]3[C:11](=[CH:10][CH:9]=2)[CH2:12][C:13]2([CH2:18][CH2:19][CH:20]([O:23][CH3:24])[CH2:21][CH2:22]2)[C:14]3=[N:32][S:30]([C:27]([CH3:29])([CH3:28])[CH3:26])=[O:31])[CH2:3]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 867067216'-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one2×

Produkt 1

HCID 86706722N-(5'-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamideAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178477244HCID 178477244, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

6′-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2′-inden]-1′(3′H)-one (Intermediate 14, 1.85 g, 5.28 mmol) and 2-methylpropane-2-sulfinamide (1.15 g, 9.50 mmol) were dissolved in 2-Me THF (40 mL). Tetraethoxytitanium (2.21 mL, 10.6 mmol) was added and the resulting mixture was heated to 80° C. over a weekend. The reaction mixture was cooled to r.t., and diluted with ethyl acetate (85 mL). Water (3 mL) was added under vigorous stirring and then the mixture was allowed to stand for 1 h. The mixture was filtered, the solvent was evaporated and the residue was purified by column chromatography on silica using a gradient of 0-70% ethyl acetate in heptanes. The product was recrystallized twice from EtOH. to give 0.750 g of the title compound (31% yield). MS (ES+) m/z 454 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to r.t.
  2. filtrationThe mixture was filtered
  3. customthe solvent was evaporated
  4. customthe residue was purified by column chromatography on silica using a gradient of 0-70% ethyl acetate in heptanes
  5. customThe product was recrystallized twice from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-7cd20821c2bc4d598944eaa3eb2446aa
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000185B2

Notizen zur Reaktion

Wird geladen…