Lithium hydroxide, monohydrate → HCID 69471865, compound

HRID 1269102Notes

Reaction equation

HRID 1269102 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][CH2:11][CH2:12][C:13]([F:16])([F:15])[CH3:14])[CH2:7][N:6]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:4].O.[OH-].[Li+]>C1COCC1.O>[C:20]([O:19][C:17]([N:6]1[CH2:7][CH:8]([CH2:10][CH2:11][CH2:12][C:13]([F:15])([F:16])[CH3:14])[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])=[O:18])([CH3:21])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69474247HCID 69474247, compound

Product 1

HCID 69471865HCID 69471865, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4,4-difluoro-pentyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (88 mg, 0.21 mmol, 1 equiv) in THF (1.2 mL) and water (0.4 mL) was added lithium hydroxide monohydrate (45 mg, 1.07 mmol, 5 equiv). The reaction mixture was stirred at rt overnight. The THF was removed under vacuum. The residue was diluted with water and washed with ether. The aqueous layer was taken up in ethyl acetate, partitioned with 10% citric acid. The organic layer was washed with water (1×), brine (1×), dried and concentrated to give 4-(4,4-difluoro-pentyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (66 mg, 96%).

Workup

  1. customThe THF was removed under vacuum
  2. additionThe residue was diluted with water
  3. washwashed with ether
  4. custompartitioned with 10% citric acid
  5. washThe organic layer was washed with water (1×), brine (1×)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c50d5036a84e442a8bc0a03ff52b35f4
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

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