Lithium hydroxide, monohydrate → HCID 69470570, compound

HRID 1269114Notes

Reaction equation

HRID 1269114 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-a5c1e45446074cd181615d1914f465ce
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

Loading…