Methyl iodide → HCID 66761556, compound

HRID 561812Notes

Reaction equation

HRID 561812 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][OH:21])[CH:16]=[CH:15][C:14]=2[CH3:22])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.[H-].[Na+].I[CH3:26]>C1COCC1>[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][O:21][CH3:26])[CH:16]=[CH:15][C:14]=2[CH3:22])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66761160HCID 66761160, compound

Product 1

HCID 66761556HCID 66761556, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl cyclopropyl[5-(2-hydroxyethyl)-2-methylbenzyl]carbamate from the previous step (1 eq.) in THF (0.2 M) was added sodium hydride (2 eq.). The resulting suspension was stirred at RT for 30 min and then added iodomethane (8 eq.). After 12 h of heating at reflux, the reaction mixture was cooled to RT and quenched with sat. aq. NH4Cl. The aqueous layer was separated and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the crude product as a colorless oil. Further purification by way of column chromatography (SiO2, Hex→7:3 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. temperatureAfter 12 h of heating
  2. temperatureat reflux
  3. temperaturethe reaction mixture was cooled to RT
  4. customquenched with sat. aq. NH4Cl
  5. customThe aqueous layer was separated
  6. extractionextracted with ether
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customConcentration of the filtrate in vacuo afforded the crude product as a colorless oil
  11. customFurther purification by way of column chromatography (SiO2, Hex→7:3 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-ee6cee4d82b043eaa2a8b0b88fbb5872
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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