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

HRID 1254984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1254984
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-8a1b5143769e42388600f099181cf1d6
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455665B2

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