Hydrochloric Acid → HCID 59536664, Verbindung

HRID 1922176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922176
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]([O:18][C:19]2[C:20]([CH3:27])=[N:21][C:22]([NH:25][CH3:26])=[CH:23][CH:24]=2)[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:9]1)=O)(C)(C)C.Cl>>[CH3:27][C:20]1[C:19]([O:18][CH:13]([C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:24][CH:23]=[C:22]([NH:25][CH3:26])[N:21]=1

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 66737795HCID 66737795, Verbindung

Produkt 1

HCID 59536664HCID 59536664, VerbindungAusbeute 12 %

Versuchsvorschrift

Stir a mixture of (3S)-3-[1-(2-methyl-6-methylamino-3-pyridyloxy)-3-methyl-butyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (S-2) and aqueous HCl (4M, 0.261 mL, 1.04 mmol) at room temperature for 1 hour. After full conversion, concentrate the mixture, dissolve in dichloromethane and load the mixture onto a pre-packed SCX column. Wash with dichloromethane followed by methanol. Release the product with 2M NH3 in methanol and concentrate under reduced pressure. Purify the crude residue by reverse phase chromatography (17-43% gradient actonitrile in 0.01 M ammoniumformate in water, 85 mL/min, for 8 min., C18 ODB XBridge column, 30×75 mm, 5 μm) to give 9 mg (12%) of (3S)-3-[1-(2-methyl-6-methylamino-3-pyridyloxy)-3-methyl-butyl]-pyrrolidine (S-2). MS (m/z)=278 [M+1].

Aufarbeitung

  1. concentrationAfter full conversion, concentrate the mixture
  2. dissolutiondissolve in dichloromethane
  3. washWash with dichloromethane
  4. concentrationconcentrate under reduced pressure
  5. customPurify the crude residue by reverse phase chromatography (17-43% gradient actonitrile in 0.01 M ammoniumformate in water, 85 mL/min, for 8 min., C18 ODB XBridge column, 30×75 mm, 5 μm)

Quellen und Nachweise

ORD-Eintrag
ord-6c61291de4464440a039ad67976ef330
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173821B2

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