Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylacetamide

HRID 2365796Notes

Reaction equation

HRID 2365796 reaction equation
C([Mg]Cl)(C)C.[Si:6]([O:13][CH2:14][C:15]([O:17]CC)=O)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].Cl.[CH3:21][NH:22][O:23][CH3:24]>C1COCC1>[Si:6]([O:13][CH2:14][C:15]([N:22]([O:23][CH3:24])[CH3:21])=[O:17])([C:9]([CH3:10])([CH3:11])[CH3:12])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 11183578Ethyl [(tert-butyldimethylsilyl)oxy]acetateHCID 178418918HCID 178418918, compound

Product 1

HCID 116010942-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylacetamideYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2M Isopropylmagnesium chloride in THF (91.6 mL, 183 mmol) was added dropwise to ethyl 2-(tert-butyldimethylsilyloxy)acetate (10.0 g, 45.8 mmol) and N,O -dimethylhydroxylamine hydrochloride (9.38 g, 96.2 mmol) in THF (500 mL) cooled in ice. The mixture was stirred for 4.5 hours allowing to slowly warm to ambient temperature. The reaction mixture was quenched with aqueous NH4Cl and concentrated to 1/3 volume. The residue was diluted with water and extracted with EtOAc. The EtOAc was washed with brine, dried over MgSO4, filtered, and evaporated to yield 2-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylacetamide (8.51 g, 36.5 mmol, 79.6% yield) as an oil.

Workup

  1. temperaturecooled in ice
  2. customThe reaction mixture was quenched with aqueous NH4Cl
  3. concentrationconcentrated to 1/3 volume
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAc
  6. washThe EtOAc was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-551d400b35ce4c3790dbb369bb30a785
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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