Lithium Hydroxide → [7-(3-Chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetic acid

HRID 711401Notes

Reaction equation

HRID 711401 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][CH:6]1[N:11]2[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[CH:14]=[C:10]2[C:9](=[O:22])[NH:8][CH2:7]1)C.[OH-].[Li+]>O1CCCC1.O>[Cl:21][C:17]1[CH:16]=[C:15]([C:13]2[CH:14]=[C:10]3[C:9](=[O:22])[NH:8][CH2:7][CH:6]([CH2:5][C:4]([OH:23])=[O:3])[N:11]3[CH:12]=2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86731547Ethyl [7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetate

Product 1

HCID 56766546[7-(3-Chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetic acidYield 85.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl[7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetate (0.573 g, 1.72 mmol) in a mixture tetrahydrofuran-water (5:1, 10 mL) was added lithium hydroxide (144 mg, 3.44 mmol) and the reaction mixture was stirred at room temperature for 18 h. The THF was evaporated and the aqueous residue diluted with H2O. The aqueous phase was acidified with hydrochloric acid (1 M) until pH<1 and a precipitation occurred; the solid was filtered, washed with water and dried under vacuum to obtain the title compound as an off-white solid (450 mg, 85% yield).

Workup

  1. customThe THF was evaporated
  2. additionthe aqueous residue diluted with H2O
  3. customa precipitation
  4. filtrationthe solid was filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6b14ff4e913a49959971a906dcd407c2
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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