Ethanol → (S)-3-[(R)-1-(2,4-Dichlorophenoxy)-2-methoxyethyl]pyrrolidine

HRID 2390569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2390569
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([OH:17])[CH2:14][O:15][CH3:16])[CH2:9]1)=O)(C)(C)C.[H-].[Na+].[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1F.CCO>CN(C=O)C.Cl>[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[O:17][C@H:13]([C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH2:14][O:15][CH3:16]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 123112Benzene, 2,4-dichloro-1-fluoro-HCID 66859300HCID 66859300, Verbindung

Produkt 1

HCID 50899618(S)-3-[(R)-1-(2,4-Dichlorophenoxy)-2-methoxyethyl]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(S)-3-((R)-1-Hydroxy-2-methoxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester (10.0 mg, 40.8 μmol) was dissolved in DMF (0.1 mL). NaH (1.5 mg, 61.1 μmol) was slowly added and the mixture was stirred at room temperature for 15 minutes. Then, 2,4-dichloro-1-fluorobenzene (20.2 mg, 122 μmol) was added. The mixture was stirred at 100° C. for 1 hour, then cooled to room temperature. The mixture was concentrated then dissolved in 1.2M HCl in EtOH (1.0 mL, 1.2 mmol) and stirred overnight at room temperature. The product was concentrated and purified by preparative HPLC to yield the title compound as a mono-TFA salt (12.8 mg, 99% purity). MS m/z: [M+H]+ calcd for C13H17Cl2NO2, 290.06; found 290.0.

Aufarbeitung

  1. stirringThe mixture was stirred at 100° C. for 1 hour
  2. temperaturecooled to room temperature
  3. concentrationThe mixture was concentrated
  4. stirringstirred overnight at room temperature
  5. concentrationThe product was concentrated
  6. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6582da0a8bd647ac977a06d82f71d2e5
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273786B2

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