Hydrochloric Acid → 4-[2-Hydroxy-3-[8-(methylamino)-3-azabicyclo[3.2.1]oct-3-yl]-propoxy}benzonitrile

HRID 411521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 411521
[C:1]([C:3]1[CH:30]=[CH:29][C:6]([O:7][CH2:8][CH:9]([OH:28])[CH2:10][N:11]2[CH2:17][CH:16]3[CH:18]([N:19](C)[C:20](=O)OC(C)(C)C)[CH:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:5][CH:4]=1)#[N:2].Cl>C(OCC)(=O)C>[OH-:7].[NH4+:2].[OH:28][CH:9]([CH2:10][N:11]1[CH2:12][CH:13]2[CH:18]([NH:19][CH3:20])[CH:16]([CH2:15][CH2:14]2)[CH2:17]1)[CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:30][CH:29]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 18540975Tert-butyl 3-[3-(4-cyanophenoxy)-2-hydroxypropyl]-3-azabicyclo-[3.2.1]oct-8-yl(methyl)carbamate

Produkt 2

HCID 14923Ammonium HydroxideHCID 185408844-[2-Hydroxy-3-[8-(methylamino)-3-azabicyclo[3.2.1]oct-3-yl]-propoxy}benzonitrileAusbeute 192,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A suspension of tert-butyl 3-[3-(4-cyanophenoxy)-2-hydroxypropyl]-3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate (see step (i) above; 3.15 g, 7.58 mmol) in ethyl acetate saturated with HCl (40 mL) was stirred for 5 h at 25° C. under nitrogen. The mixture was partitioned with water (100 mL) and ethyl acetate (50 mL). The aqueous layer was separated and washed with ethyl acetate. The aqueous layer was separated, basified with saturated sodium bicarbonate (30 mL) and then extracted with dichloromethane (3×50 mL). The organic extracts were dried (Na2SO4), filtered, concentrated in vacuo and then chromatographed on silica gel, eluting with dichloromethane:methanol:concentrated ammonium hydroxide (88:10:2), to afford 2.30 g (96%) of the title compound as a colorless oil.

Aufarbeitung

  1. customThe mixture was partitioned with water (100 mL) and ethyl acetate (50 mL)
  2. customThe aqueous layer was separated
  3. washwashed with ethyl acetate
  4. customThe aqueous layer was separated
  5. extractionextracted with dichloromethane (3×50 mL)
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica gel
  10. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-1c50fa3ccae14ad08327660253e16939
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559162B2

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