Lithium hydroxide, monohydrate → HCID 69670118, compound

HRID 2038206Notes

Reaction equation

HRID 2038206 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([CH:8]1[CH2:12][C:11](=[O:13])[N:10]([CH:14]2[CH2:19][CH:18]([CH3:20])[CH2:17][CH2:16][CH:15]2[CH:21]([CH3:23])[CH3:22])[CH2:9]1)=[O:7]>O1CCCC1>[CH:21]([CH:15]1[CH2:16][CH2:17][CH:18]([CH3:20])[CH2:19][CH:14]1[N:10]1[C:11](=[O:13])[CH2:12][CH:8]([C:6]([OH:7])=[O:5])[CH2:9]1)([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69670044HCID 69670044, compound

Product 1

HCID 69670118HCID 69670118, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide, monohydrate (LiOH, H2O) (13.22 g, 0.315 mol) was added to a solution of 1-(2-isopropyl-5-methyl-cyclohexyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (obtained as in EXAMPLE I, 59 g, 0.21 mol,) in a mixture of tetrahydrofuran (THF:H2O:CH3OH) (1:1:1) (300 mL) at room temperature and was stirred for 1-2 hours. THF and CH3OH were then removed via evaporation. HCl was added and the reaction mixture was extracted three times with ethyl acetate. The organic fractions were combined, washed with brine, dried, and concentrated to provide 1-(2-isopropyl-5-methyl-cyclohexyl)-5-oxo-pyrrolidine-3-carboxylic acid (50 g), which was further evaporated with benzene twice to remove traces of water.

Workup

  1. customTHF and CH3OH were then removed via evaporation
  2. additionHCl was added
  3. extractionthe reaction mixture was extracted three times with ethyl acetate
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea1fd75c5e45473588a4b1d9e7cff862
Source dataset
uspto-grants-2013_11
Patent number
US08575349B2

Reaction notes

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