Methyl iodide → HCID 58358782, compound

HRID 1626304Notes

Reaction equation

HRID 1626304 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:26]>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH3:26])[C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57260263HCID 57260263, compound

Product 1

HCID 58358782HCID 58358782, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of benzyl 3-(tert-butyldimethylsilyloxy)propylcarbamate obtained in step 2 (5 g, 15.5 mmol) in tetrahydrofuran (20 ml), sodium hydride (1.24 g, 31 mmol, 60% in mineral oil) and iodomethane (3.86 ml, 62 mmol) were added slowly. The reaction temperature was warmed up to room temperature, and stirred for overnight. The reaction was completed quenched by water and organic material was extracted with ether. After evaporation of volatile material under reduced pressure, the residue was purified with silica gel column chromatography (EtOAC:Hx=1:10) to give the title compound (4.9 g, 94%) as light yellow oil.

Workup

  1. customThe reaction was completed quenched by water and organic material
  2. extractionwas extracted with ether
  3. customAfter evaporation of volatile material under reduced pressure
  4. customthe residue was purified with silica gel column chromatography (EtOAC:Hx=1:10)

Sources & evidence

ORD record
ord-1ae3437e742d4669b3a669522daff2fc
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Reaction notes

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