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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 1022372
Notes
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Reaction equation

HRID 1022372 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=O)C>[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 DMF a solution of 4-[2-(2,5-dimethyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester in 10 ml DMF is added at a temperature of 60° C. After stirring for 3 h at 60° C. the reaction mixture is evaporated. The residue is diluted with 10 ml water, neutralized with 10% hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and evaporated to give 3-(2,5-dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one as a light brown resin. This material is triturated with diethyl ether/hexane, filtered and dried to afford a solid, mp: 176-177° C.

Workup

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

Sources & evidence

ORD record
ord-fa8fd640ca37408db49ed3078be72c23
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722578B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes