Methyl iodide → HCID 178486067, compound

HRID 577741Notes

Reaction equation

HRID 577741 reaction equation
[CH3:1][C:2]([Si:17]([CH3:20])([CH3:19])[CH3:18])([O:4][C@@H:5]1[CH2:8][C@H:7]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6]1)[CH3:3].[H-].[Na+].I[CH3:24]>C1COCC1>[CH3:24][N:9]([C@H:7]1[CH2:6][C@@H:5]([O:4][C:2]([CH3:1])([Si:17]([CH3:20])([CH3:19])[CH3:18])[CH3:3])[CH2:8]1)[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178454133HCID 178454133, compound

Product 1

HCID 178486067HCID 178486067, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude tert-butyl {cis-3-[1-methyl-1-(trimethylsilyl)ethoxy]cyclobutyl}carbamate (108 g) in THF (1 L) was added NaH (60% in oil, 39.6 g, 0.99 mol) in portions and the resulting mixture was stirred at rt for 30 min. The mixture was then cooled to 0° C. and iodomethane (140.58 g, 0.99 mol) was added dropwise. After addition, the mixture was stirred from 0° C. to rt overnight. The mixture was quenched with sat. NH4Cl, and water was added (200 mL), and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, then evaporated to give crude product which was purified via silica gel chromatography to give the title compound (68.9 g, 87% yield) as an oil.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. additionAfter addition
  3. stirringthe mixture was stirred from 0° C. to rt overnight
  4. customThe mixture was quenched with sat. NH4Cl, and water
  5. additionwas added (200 mL)
  6. extractionextracted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customto give crude product which
  11. customwas purified via silica gel chromatography

Sources & evidence

ORD record
ord-a2b4bf82bb80432ea18a733d37b77b94
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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