Methyl iodide → HCID 14194550, compound

HRID 453888Notes

Reaction equation

HRID 453888 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].CI.[CH3:24]COC(C)=O.CCCCCC>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH3:24])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14040059HCID 14040059, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 14194550HCID 14194550, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

50 g (1 eq.) tert-butyl 3-(tert-butyldimethylsilyloxy)propylcarbamate dissolved in 200 ml THF were added dropwise to a mixture of 20.7 g (5 eq.) sodium hydride and 300 ml THF at 0° C. After heating the reaction mixture to 10° C., 32.3 ml (3 eq.) methyl iodide were added dropwise. On completion of the addition, the mixture was stirred for 3 h at room temperature. The reaction course was monitored by thin-layer chromatography (30% EtOAc/hexane). Once the conversion was complete, the reaction mixture was quenched with saturated NH4Cl solution and then extracted with ethyl acetate. The combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure, 48 g (92%) of product were obtained in the form of an oil.

Workup

  1. additionOn completion of the addition
  2. customthe reaction mixture was quenched with saturated NH4Cl solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customremoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-9f083ed3f0564b96918bdac3d5567773
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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