Lithium Hydroxide → HCID 42641538, compound

HRID 2382200Notes

Reaction equation

HRID 2382200 reaction equation
[C:1]1([CH:7]([C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)[CH:8]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([O:16]C)=[O:15])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+]>C1COCC1.O>[C:1]1([CH:7]([C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)[CH:8]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68734256HCID 68734256, compound

Product 1

HCID 42641538HCID 42641538, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(3-(phenyl(m-tolyl)methyl)pyrrolidin-1-yl)acetate (1.5 g, 4.64 mmol) in THF at 0° C. was added a solution of lithium hydroxide (0.58 g, 13.8 mmol) in water and the reaction mixture was stirred for 4 h. The reaction mixture was concentrated under reduced pressure. To the residue was added water, the pH of the aqueous layer was adjusted to 3 using dil.HCl and extracted with 30% methanol in chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 0.72 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added water
  3. extractionHCl and extracted with 30% methanol in chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d563ff119d5f4a4b8be24c6fc1a0ea4a
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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