Lithium Hydroxide → 1-(3-Pyridinylcarbonyl)proline

HRID 82489Notes

Reaction equation

HRID 82489 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 31027361-(3-Pyridinylcarbonyl)prolineYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-1e2831d541734e3f8668c0d8cccacdd9
Source dataset
uspto-grants-2014_09
Patent number
US08846721B2

Reaction notes

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