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Trimethylsilyldiazomethane → N-BOC-1,3-dihydro-2H-isoindole-1-carboxylic acid, methyl ester

HRID 23880
Notes
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Reaction equation

HRID 23880 reaction equation
[C:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:17]([OH:19])=[O:18])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:20][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[C:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:17]([O:19][CH3:20])=[O:18])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27559672-((tert-butoxy)carbonyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid

Product 1

HCID 57984733N-BOC-1,3-dihydro-2H-isoindole-1-carboxylic acid, methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-BOC-1,3-dihydro-2H-isoindol-1-carboxylic acid (SNPE, 10 g, 38 mmol) in CH2Cl2 (100 mL) and MeOH (100 mL) at 0° C. was added trimethylsilyldiazomethane dropwise until the yellow color persisted. After stirring at rt for 15 min, the reaction mixture was concentrated in vacuo. The residue was azeotroped with toluene to afford N-BOC-1,3-dihydro-2H-isoindol-1-carboxylic acid, methyl ester which was used without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-c52fefe22e2640288025b208c38064ec
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855708B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes