Methyl iodide → HCID 59020123, compound

HRID 971148Notes

Reaction equation

HRID 971148 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CI.[H-].[Na+].[CH3:23]COC(C)=O>C1COCC1.O>[C:1]([O:5][C:6](=[O:18])[N:7]([C:8]1([C:11]2[CH:12]=[CH:13][C:14]([I:17])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1)[CH3:23])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 59019959tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamate

Product 1

HCID 59020123HCID 59020123, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Part A. 1-(4-Iodophenyl)cyclopropyl-carbamic acid tert-butyl ester (2.14 g, 5.85 mmol) was stirred in THF (20 mL) at 0° C. under N2. MeI (3 mL) was added followed by portionwise addition of NaH (2.34 g, 5 eq). The reaction was stirred at rt overnight. Several drops of H2O and EtOAc (20 mL) were added to quench the reaction. The organic solvent was evaporated, and H2O was added. It was extracted with Et2O (2×), washed with brine, dried over MgSO4, and concentrated to dryness. The residue was purified by FCC (silica gel, CH2Cl2:hexanes=0:1 to 1:1 to 1:0) to give pure [1-(4-iodophenyl)cyclopropyl]-methyl-carbamic acid tert-butyl ester as a white solid (2.07 g, yield 95%). LC/MS (ESI+) 373.8 (M+H), tR=2.95 min (10–90% CH3CN in H2O in a 4-min run).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic solvent was evaporated
  4. additionH2O was added
  5. extractionIt was extracted with Et2O (2×)
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by FCC (silica gel, CH2Cl2:hexanes=0:1 to 1:1 to 1:0)

Sources & evidence

ORD record
ord-a401d52b00ca4ee092edf6dc12659914
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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