Hydrochloric Acid → 1-{[4-(2-tert-Butylphenyl)piperazin-1-yl](oxo) acetyl}pyrrolidine-3-carboxylic acid

HRID 534984Notes

Reaction equation

HRID 534984 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[C:18]([N:20]2[CH2:24][CH2:23][CH:22]([C:25]([O:27]C)=[O:26])[CH2:21]2)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[C:18]([N:20]2[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=[O:26])[CH2:21]2)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66753001HCID 66753001, compound

Product 1

HCID 667510291-{[4-(2-tert-Butylphenyl)piperazin-1-yl](oxo) acetyl}pyrrolidine-3-carboxylic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 1-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}pyrrolidine-3-carboxylate (Example 190, 0.32 g, 0.80 mmol) and 1 M LiOH solution (5 mL, 5.0 mmol) in tetrahydrofuran (5 mL) was stirred at room temperature for 3 h. The reaction mixture was acidified with 1 M HCl solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.29 g, 92%) as a white amorphous. It was crystallized from diisopropyl ether-ethyl acetate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3a02ae2fc4546568ce9b405249b5402
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

Loading…