Lithium hydroxide, monohydrate → HCID 69470570, compound

HRID 1374472Notes

Reaction equation

HRID 1374472 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][C:8]([CH2:11][CH2:12][CH2:13][CH3:14])([F:10])[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:4].O.[OH-].[Li+]>C1COCC1.O>[C:18]([O:17][C:15]([N:6]1[CH2:7][C:8]([CH2:11][CH2:12][CH2:13][CH3:14])([F:10])[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])=[O:16])([CH3:19])([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69473620HCID 69473620, compound

Product 1

HCID 69470570HCID 69470570, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-butyl-4-fluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (270 mg, 0.89 mmol) in THF (12 mL) and water (4 mL), was added lithium hydroxide monohydrate (45 mg, 1.07 mmol). The reaction mixture was stirred at room temperature for 16 hours. THF was removed under vacuum and the residue was taken up in ethyl acetate (150 mL), washed with 10% citric acid (100 mL) and brine (20 mL). Removal of solvent provided 4-butyl-4-fluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (260 mg, 100%).

Workup

  1. customTHF was removed under vacuum
  2. washwashed with 10% citric acid (100 mL) and brine (20 mL)
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-7a89ccae51d645ccb93c343743668719
Source dataset
uspto-grants-2007_01
Patent number
US07164011B2

Reaction notes

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