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Sodium Methoxide → 3-(2,5-Dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

HRID 1962360
Notes
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Reaction equation

HRID 1962360 reaction equation
C[O-].[Na+].C[O:5][C:6]([C:8]1([NH:16][C:17](=[O:27])[CH2:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=2[CH3:26])[CH2:13][CH2:12][N:11]([O:14][CH3:15])[CH2:10][CH2:9]1)=O>CN(C)C=O>[CH3:26][C:20]1[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:19]=1[C:18]1[C:17](=[O:27])[NH:16][C:8]2([CH2:9][CH2:10][N:11]([O:14][CH3:15])[CH2:12][CH2:13]2)[C:6]=1[OH:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 44603928Methyl 4-[2-(2,5-dimethyl-phenyl)acetylamino]-1-methoxy-piperidine-4-carboxylate

Product 1

HCID 547422463-(2,5-Dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To 0.82 g of sodium methylate in 20 ml of dimethylformamide was added a solution of 4-[2-(2,5-dimethyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester in 10 ml of dimethylformamide at a temperature of 60° C. After stirring for 3 hours at 60° C., the reaction mixture was evaporated. The residue was diluted with 10 ml of water, neutralized with 10% hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and evaporated to yield 1.23 g of 3-(2,5-dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one (compound C1) as a light brown resin. This material was triturated with diethyl ether/hexane, filtered and dried to afford a solid, mp: 176-177° C.

Workup

  1. customthe reaction mixture was evaporated
  2. additionThe residue was diluted with 10 ml of water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4679bace28174cca9fc6658b4dc19cfb
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415369B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes