Lithium Hydroxide → 1-(3-Pyridinylcarbonyl)proline

HRID 82489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82489
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:11])=[O:4].[OH-].[Li+]>C1COCC1.O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:10]([N:6]2[CH2:7][CH2:8][CH2:9][CH:5]2[C:3]([OH:4])=[O:2])=[O:11])[CH:13]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 434099981-(Pyridine-3-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester

Produkt 1

HCID 31027361-(3-Pyridinylcarbonyl)prolineAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 1-(pyridine-3-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester (1.3 g, 5.4 mmol), in THF (13 mL) was added lithium hydroxide (0.34 g, 8.1 mmol) in water (1.3 mL) at room temperature (25° C.). The mixture was allowed to stir at room temperature (25° C.) over a period of 2 h. THF was evaporated from the reaction mixture, dissolve the residue in methanol acidified to pH=4, filtered and evaporated the sticky liquid on evaporation was triturated with diethyl ether, to obtain required compound as off-white solid (1.0 g, 83%).

Aufarbeitung

  1. customTHF was evaporated from the reaction mixture
  2. dissolutiondissolve the residue in methanol
  3. filtrationfiltered
  4. customevaporated the sticky liquid
  5. customon evaporation
  6. customwas triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1e2831d541734e3f8668c0d8cccacdd9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846721B2

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