Ethanol → (S)-3-[(R)-2-Ethoxy-1-(naphthalen-1-yloxy)ethyl]pyrrolidine

HRID 1254988

Reaktionsgleichung

Reaktionsgleichung von HRID 1254988
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([OH:18])[CH2:14][O:15][CH2:16][CH3:17])[CH2:9]1)=O)(C)(C)C.F[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.[H-].[Na+].CCO>CN(C=O)C.Cl>[CH2:16]([O:15][CH2:14][C@@H:13]([C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[O:18][C:28]1[C:29]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][CH:27]=1)[CH3:17]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 94501-FluoronaphthaleneHCID 24758Sodium hydrideHCID 66858889(S)-3-((R)-2-Ethoxy-1-hydroxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

Produkt 1

HCID 58120253(S)-3-[(R)-2-Ethoxy-1-(naphthalen-1-yloxy)ethyl]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(S)-3-((R)-2-Ethoxy-1-hydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester (200 mg, 0.8 mmol) and 1-fluoronaphthalene were dissolved in DMF (2.7 mL). NaH (27.8 mg, 1.2 mmol) was added and the mixture was stirred at room temperature for 15 minutes, then heated at 120° C. for 4 hours. The mixture was then cooled to room temperature. The mixture was concentrated then dissolved in 1.2M HCl in EtOH (19 mL, 23 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 (125 mg, 94% purity). MS m/z: [M+H]+ calcd for C18H23NO2, 286.17. found 286.2.

Aufarbeitung

  1. temperatureheated at 120° C. for 4 hours
  2. temperatureThe mixture was then cooled 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-a65eff7169bf408592aa37e25a9f1384
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455665B2

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