Hydrochloric Acid → 5-Oxo-1-(3-pyrrol-1-yl-propyl)-pyrrolidine-3-carboxylic acid

HRID 2281619Notes

Reaction equation

HRID 2281619 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH2:6]1)=[O:4].Cl>C1COCC1.[Li+].[OH-]>[O:10]=[C:8]1[N:7]([CH2:11][CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 671207165-Oxo-1-(3-pyrrol-1-yl-propyl)-pyrrolidine-3-carboxylic acid methyl ester

Product 1

HCID 671206895-Oxo-1-(3-pyrrol-1-yl-propyl)-pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (0° C.) of 5-Oxo-1-(3-pyrrol-1-yl-propyl)-pyrrolidine-3-carboxylic acid methyl ester in THF, 0.2M LiOH is added and RM is stirred for 3 hours gradually warming to room temperature. Reaction mixture is acidified with 1N HCl and product extracted into ethyl acetate. The organic phase is washed with brine, dried over magnesium sulphate and the solvent evaporated in vacuo to yield 5-Oxo-1-(3-pyrrol-1-yl-propyl)-pyrrolidine-3-carboxylic acid.

Workup

  1. customReaction mixture
  2. extractionextracted into ethyl acetate
  3. washThe organic phase is washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-9e3002316afb4be09f21f099f29ee0bf
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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