Potassium Carbonate → HCID 66738591, Verbindung

HRID 1691861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691861
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@H:20]([NH2:23])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@H:20]([NH:23][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate2×

Produkt 1

HCID 66738591HCID 66738591, VerbindungAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-5-nitro-pyridine (3.4 g, 0.021 mol), (S)-(−)-3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester (4 g, 0.021 mol), and potassium carbonate (14.5 g, 0.105 mol) in acetonitrile (50 mL) was heated at reflux for 24 h. The reaction was monitored by LCMS and additional (S)-(−)-3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester was added until the reaction was driven to completion. The reaction mixture was then filtered and concentrated to give (S)-3-(5-nitro-pyridin-2-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (5.1 g, 78.6%) as a yellow solid. LCMS calcd for C14H20N4O4 (m/e) 308, obsd 307.1 (M−H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. additionwas added until the reaction
  4. filtrationThe reaction mixture was then filtered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a7c4e259781f4de8ba08cdf3e9f1245a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153644B2

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