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

HRID 1774150Notes

Reaction equation

HRID 1774150 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 ⅓ 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
  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-a37692d95c1342a2949d616c841d66f9
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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