Lithium Hydroxide → HCID 66750856, compound

HRID 534914Notes

Reaction equation

HRID 534914 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:24])[CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].CO.O.CC#N.O>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:24])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 18373917Acetonitrile--water (1/1)HCID 22242641Methanol--water (1/1)HCID 66750827Methyl 4-(4-(2-tert-butylphenyl)-piperazin-1-yl)-4-oxobutanoate

Product 1

HCID 66750856HCID 66750856, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-(4-(2-tert-butylphenyl)-piperazin-1-yl)-4-oxobutanoate obtained in Example 52 (0.245 g, 0.74 mmol) in THF (2.0 mL) was added a solution of lithium hydroxide (0.053 g, 2.20 mmol) in 4:1 MeOH/H2O (2.5 mL) at room temperature. After 2 h the reaction mixture was concentrate under reduced pressure. The residue was acidified to pH 1-2 with 1.0 M hydrochloric acid and extracted with ethyl acetate (3×20 mL). The combined organics were washed with saturated sodium chloride (20 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to provide a residue. Trituration of the residue with 1:3 CH3CN/H2O provided 4-(4-(2-tert-butylphenyl)piperazin-1-yl)-4-oxobutanoic acid (0.217 g, 92%) as a white solid, mp 175-176° C.

Workup

  1. concentrationAfter 2 h the reaction mixture was concentrate under reduced pressure
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organics were washed with saturated sodium chloride (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide a residue

Sources & evidence

ORD record
ord-13440f9556db4301827fce8e178fbab8
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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