Hydrochloric Acid → 6'-(3-Fluoropropoxy)-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

HRID 539332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539332
Cl.[F:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][C:11]1([CH2:20][CH2:19][CH:18]([O:21][CH3:22])[CH2:17][CH2:16]1)[C:10]2=[N:23]S(C(C)(C)C)=O>O1CCOCC1.C([O-])(O)=O.[Na+]>[F:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13]([CH2:12][C:11]3([CH2:16][CH2:17][CH:18]([O:21][CH3:22])[CH2:19][CH2:20]3)[C:10]2=[NH:23])=[CH:14][CH:15]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 67979469N-(5'-(3-Fluoropropoxy)-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-yhdene)-2-methylpropane-2-sulfinamide

Produkt 1

HCID 679795506'-(3-Fluoropropoxy)-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imineAusbeute 111,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

HCl (4 M in 1,4-dioxane, 1.489 mL, 5.96 mmol) was added to a solution of N-(5′-(3-fluoro-propoxy)-4-methoxyspiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Example 20v, Step 1, 244 mg, 0.60 mmol) in anhydrous 1,4-dioxane (25 mL). A white precipitate was formed immediately and the resulting cloudy mixture was stirred under a nitrogen atmosphere overnight. The mixture was diluted with NaHCO3 (aq) and extracted with DCM, dried over MgSO4 and concentrated in vacuo to give 204 mg (quantitative yield) of the title compound that was used without any purification in the next step: MS (ES+) m/z 306 [M+H]+.

Aufarbeitung

  1. customA white precipitate was formed immediately
  2. extractionextracted with DCM
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b5231571552a4faf9098e9c591663713
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865911B2

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