Lithium hydroxide, monohydrate → HCID 69471954, compound

HRID 1269105Notes

Reaction equation

HRID 1269105 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][CH2:11][C:12]([F:16])([F:15])[CH2:13][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][C:12]([F:15])([F:16])[CH2:13][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 69469846HCID 69469846, compound

Product 1

HCID 69471954HCID 69471954, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3,3-difluoro-pentyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (106 mg, 0.26 mmol, 1 equiv) in THF (2.4 mL) and water (0.8 mL) was added lithium hydroxide monohydrate (54 mg, 1.29 mmol, 5 equiv). The reaction mixture was stirred at rt overnight. THF was removed under vacuum. The residue was diluted with water (10 mL), washed with ether (20 mL). The aqueous layer was taken up in ethyl acetate (50 mL), partitioned with 10% citric acid (25 mL). The organic layer was washed with water (1×), brine (1×), dried and concentrated to give 4-(3,3-difluoro-pentyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester as a clear oil (82.1 mg, 99%).

Workup

  1. customTHF was removed under vacuum
  2. additionThe residue was diluted with water (10 mL)
  3. washwashed with ether (20 mL)
  4. custompartitioned with 10% citric acid (25 mL)
  5. washThe organic layer was washed with water (1×), brine (1×)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-eddb538d8b1c40e1994d1694dbb467d5
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

Loading…