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Methyl p-toluenesulfonate → 5-Benzyl-7-methoxy-5-azaspiro[2.4]heptane

HRID 1010801
Notes
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Reaction equation

HRID 1010801 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]([OH:15])[C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].S(OC)([C:21]1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[CH2:1]([N:8]1[CH2:14][CH:13]([O:15][CH3:21])[C:10]2([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 584529235-Benzyl-5-azaspiro[2.4]heptan-7-ol

Product 1

HCID 167382885-Benzyl-7-methoxy-5-azaspiro[2.4]heptane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5-Benzyl-5-azaspiro[2.4]heptan-7-ol (200 mg) was dissolved into DMF (4 ml) and cooled at 0° C. NaH (120 mg) was added to the reaction and stirred for 10 minutes. To the reaction was added TsOMe (200 mg), the solution was heated at 80° C. for two hours. The reaction was quenched with water and extracted with EtOAc followed by washing with water, then brine and dried over Na2SO4 and evaporated to give the titled product. Mass: (M+1), 158

Workup

  1. temperaturethe solution was heated at 80° C. for two hours
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washby washing with water
  5. dry with materialbrine and dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-f54aada8aa714135bf3a53651debd1bd
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977346B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes