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

HRID 411746Notes

Reaction equation

HRID 411746 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]

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-isoindole-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 to dryness, and the residue was azeotroped with toluene to yield N-BOC-1,3-dihydro-2H-isoindole-1-carboxylic acid, methyl ester which was used without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo to dryness
  2. customthe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-aad8f73f75374e37be938d799ad33cf6
Source dataset
uspto-grants-2003_05
Patent number
US06559174B2

Reaction notes

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