Lithium hydroxide, monohydrate → HCID 68537795, compound

HRID 1442967Notes

Reaction equation

HRID 1442967 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH:5]=[C:6]1[CH2:10][N:9]([C:11]([OH:13])=[O:12])[CH:8]([C:14]([OH:16])=[O:15])[CH2:7]1.O.[OH-].[Li+]>O1CCCC1.O>[C:4]([O:12][C:11]([N:9]1[CH2:10][C:6](=[CH:5][C:4]2[CH:17]=[CH:18][CH:19]=[C:2]([F:1])[CH:3]=2)[CH2:7][CH:8]1[C:14]([OH:16])=[O:15])=[O:13])([CH3:17])([CH3:5])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69729930HCID 69729930, compound

Product 1

HCID 68537795HCID 68537795, compoundYield 153.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(3-Fluoro-benzylidene)-pyrrolidine-1,2-dicarboxylic acid 1-terf butyl ester 2-methyl ester (3.23 g, 9.63 mmol) in tetrahydrofuran (150 ml), was added 1M lithium hydroxide monohydrate (1.21 g, 28.9 mmol) in water (50 ml). The mixture was stirred at room temperature for 3 days. Tetrahydrofuran was removed by evaporation under reduced pressure, the residue diluted with water (30 ml) and acidified to pH 2.0-3.0 using 1M hydrochloric acid. The aqueous was extracted with diethyl ether (3×100 ml) and the combined organics dried over magnesium sulfate. The solvent was removed by evaporation under reduced pressure to give the title compound (2.37 g, 77%) as a white foam.

Workup

  1. customTetrahydrofuran was removed by evaporation under reduced pressure
  2. additionthe residue diluted with water (30 ml)
  3. extractionThe aqueous was extracted with diethyl ether (3×100 ml)
  4. dry with materialthe combined organics dried over magnesium sulfate
  5. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-947f058396534d4aa4b9154b30213631
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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