Lithium hydroxide, monohydrate → 3-Phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid

HRID 1013338Notes

Reaction equation

HRID 1013338 reaction equation
C([O:3][C:4]([CH:6]1[CH2:21][CH2:20][C:9]2([O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10]2)[CH2:8][CH2:7]1)=[O:5])C.O.[OH-].[Li+]>CO.O>[C:14]1([C:11]2[CH2:10][C:9]3([CH2:20][CH2:21][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]3)[O:13][N:12]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57951452HCID 57951452, compound

Product 1

HCID 579514503-Phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid ethyl ester (190 mg, 0.67 mmol) in MeOH (5 ml) and lithium hydroxide monohydrate (74 mg, 1.0 mmol) in H2O (1 ml) was stirred overnight at RT. After removal of the solvent under vacuum, the residue was taken up in 10% aq. citric acid solution and EtOAc and the phases were separated. The aqueous phase was extracted several times with EtOAc, dried over magnesium sulphate and desolventised under vacuum. 150 g (87% of the theoretical amount) of the free acid 3-phenyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid was obtained in the form of a colourless solid.

Workup

  1. customAfter removal of the solvent under vacuum
  2. customEtOAc and the phases were separated
  3. extractionThe aqueous phase was extracted several times with EtOAc
  4. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-25baa657ff744d4cb94053428a456885
Source dataset
uspto-grants-2011_07
Patent number
US07981883B2

Reaction notes

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