Lithium hydroxide, monohydrate → HCID 69472782, compound

HRID 1374463Notes

Reaction equation

HRID 1374463 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 8028TetrahydrofuranSolvent2×

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. customwas 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-87f0aef919034652bde581e952b7c041
Source dataset
uspto-grants-2007_01
Patent number
US07164011B2

Reaction notes

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