Dimethylformamide → [(R)-1-(4-Cyanophenyl)pyrrolidin-3-yl]carbamic Acid

HRID 2251299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251299
C(OC(N[N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)=O)(C)(C)C.F[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.[C:23](=[O:26])([O-])[O-:24].[Cs+].[Cs+].C[N:30](C=O)C>O.C(OCC)(=O)C>[C:19]([C:18]1[CH:21]=[CH:22][C:15]([N:9]2[CH2:10][CH2:11][C@@H:12]([NH:30][C:23](=[O:26])[OH:24])[CH2:13]2)=[CH:16][CH:17]=1)#[N:20]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 145174-FluorobenzonitrileHCID 21959621Tert-butyl pyrrolidin-1-ylcarbamate

Produkt 1

HCID 68574711[(R)-1-(4-Cyanophenyl)pyrrolidin-3-yl]carbamic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of (3R)-(+)-(tert-butoxycarbonylaminopyrrolidine (1.0 g), p-fluorobenzonitrile (650 mg), cesium carbonate (1.75 g) and 5 ml of DMF was stirred at 50° C. for 12 h. Ethyl acetate and water were then added to the reaction solution, and the organic phase was washed twice with water, dried over sodium sulfate and filtered, and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way; MS (ESI): 288.20 (M+H+).

Aufarbeitung

  1. washthe organic phase was washed twice with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by preparative HPLC
  6. customThe product with the molecular weight of 287.36 (C16H21N3O2) was obtained in this way

Quellen und Nachweise

ORD-Eintrag
ord-24ca460457ba4194abbf8b76cadf8e68
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319108B2

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