Methyl iodide → HCID 60051172, compound

HRID 23881Notes

Reaction equation

HRID 23881 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]([O:19][CH3:20])=[O:18])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CI.[Li+].[CH3:24]C([N-]C(C)C)C>C1COCC1>[C:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1([CH3:24])[C:17]([O:19][CH3:20])=[O:18])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 57984733N-BOC-1,3-dihydro-2H-isoindole-1-carboxylic acid, methyl ester

Product 1

HCID 60051172HCID 60051172, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution N-BOC-1,3-dihydro-2H-isoindol-1-carboxylic acid, methyl ester (38 mmol) and MeI (10 mL, 160 mmol) in 150 mL of anhydrous THF at −30° C. was added LDA (Aldrich, 1.5 M in cyclohexane, 51 mL, 76.5 mmol). The reaction was allowed to warm up to rt over 4 h. The reaction was cooled to −30° C., and was quenched with saturated aqueous solution of NH4Cl (50 mL). The resulting mixture was partitioned between EtOAc and brine, and the product was extracted with EtOAc (3×100 mL). The combined extracts were dried with anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted with 10:1 to 5:1 hexane/ether to afford N-BOC-1-methyl-1,3-dihydro-2H-isoindol-1-carboxylic acid, methyl ester.

Workup

  1. temperatureThe reaction was cooled to −30° C.
  2. customwas quenched with saturated aqueous solution of NH4Cl (50 mL)
  3. customThe resulting mixture was partitioned between EtOAc and brine
  4. extractionthe product was extracted with EtOAc (3×100 mL)
  5. dry with materialThe combined extracts were dried with anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluted with 10:1 to 5:1 hexane/ether

Sources & evidence

ORD record
ord-1a22d7a87ec242e28e7614dc70e47c44
Source dataset
uspto-grants-2005_02
Patent number
US06855708B2

Reaction notes

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