Lithium hydroxide, monohydrate → HCID 69472782, compound

HRID 1269104Notes

Reaction equation

HRID 1269104 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][CH2:11][C:12]([F:15])([F:14])[CH3:13])[CH2:7][N:6]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:4].O.[OH-].[Li+]>C1COCC1.O>[C:19]([O:18][C:16]([N:6]1[CH2:7][CH:8]([CH2:10][CH2:11][C:12]([F:14])([F:15])[CH3:13])[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])=[O:17])([CH3:20])([CH3:21])[CH3:22]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69470507HCID 69470507, compound

Product 1

HCID 69472782HCID 69472782, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(3,3-difluoro-butyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (92.7 mg, 0.23 mmol, 1 equiv) in THF (1.2 mL) and water (0.4 mL) was added lithium hydroxide monohydrate (49 mg, 1.17 mmol, 5 equiv). The reaction mixture was stirred at rt overnight. the THF was removed under vacuum. The residue was diluted with water, 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 a white solid, 4-(3,3-difluoro-butyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (59.7 mg, 83%).

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-d70e0904c8b8461aacf80365150a8577
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

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