Hydrochloric Acid → (S)-3-Methoxy-5-(2-methylpyrrolidin-1-YL)aniline

HRID 1410109

Reaktionsgleichung

Reaktionsgleichung von HRID 1410109
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:17])[CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1.Cl>O1CCOCC1.O.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[C:5]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:17])[CH:4]=1

Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 68379376(S)-1-(3-methoxy-5-nitrophenyl)-2-methylpyrrolidine

Produkt 1

HCID 68379440(S)-3-Methoxy-5-(2-methylpyrrolidin-1-YL)anilineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of (S)-1-(3-methoxy-5-nitrophenyl)-2-methylpyrrolidine (430 mg, 1.82 mmol) and Zinc (1.18 g, 18.2 mmol) in dioxane (20 mL) and H2O (10 mL) was added dropwise conc. HCl (1.8 mL) at room temperature, and the mixture was stirred for 2 h. The reaction mixture was filtered and the filtrate was adjusted to pH˜8 by the addition of solid NaHCO3, and then extracted with ethyl acetate (50 mL). The organic layer was dried with Na2SO4, concentrated and the residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to afford (S)-3-methoxy-5-(2-methylpyrrolidin-1-yl)benzenamine (269 mg, 72%) as yellow oil. LC-MS: 207 [M+H]+, tR=1.193 min.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was adjusted to pH˜8 by the addition of solid NaHCO3
  3. extractionextracted with ethyl acetate (50 mL)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-f8d915773dc9436199ac78d19d08a571
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921383B2

Verknüpfte Notizen

Wird geladen…