Ethanol → (S)-3-[(R)-1-(4-Chloro-2-methylphenoxy)-2-methylsulfanylethyl]pyrrolidine

HRID 1254992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1254992
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([OH:17])[CH2:14][S:15][CH3:16])[CH2:9]1)=O)(C)(C)C.[H-].[Na+].[Cl:20][C:21]1[CH:22]=[CH:23][C:24](F)=[C:25]([CH3:27])[CH:26]=1.CCO>CN(C=O)C.Cl>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:17][C@H:13]([C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:14][S:15][CH3:16])=[C:25]([CH3:27])[CH:26]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 27251135-Chloro-2-fluorotolueneHCID 66859519(S)-3-((R)-1-Hydroxy-2-methylsulfanylethyl)pyrrolidine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 58120257(S)-3-[(R)-1-(4-Chloro-2-methylphenoxy)-2-methylsulfanylethyl]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(S)-3-((R)-1-Hydroxy-2-methylsulfanylethyl)pyrrolidine-1-carboxylic acid t-butyl ester (20 mg, 80 μmol) was dissolved in DMF (367 μL). NaH (3.7 mg, 153 μmol) was added and the mixture was stirred at room temperature for 15 minutes. 5-Chloro-2-fluorotoluene (33.2 mg mg, 230 tμmol) was added and the mixture was stirred at 100° C. for 1 hour. The mixture was cooled to room temperature, concentrated then dissolved in 1.2M HCl in EtOH (2.2 mL, 2.7 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 (0.6 mg, purity 85%). MS m/z: [M+H]+ calcd for C14H20ClNOS, 286.10. found 286.0.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-449d036d5a25445e86a5e1172edd1c74
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455665B2

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