Methyl iodide → HCID 86705495, compound

HRID 2279492Notes

Reaction equation

HRID 2279492 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:21]1COCC1.[H-].[Na+].CI>O>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH2:10][CH2:11][O:12][CH3:21])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 27281741HCID 27281741, compound

Product 1

HCID 86705495HCID 86705495, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 174 (2.22 g, 6.93 mmol) and THF (30 mL).cooled to 0° C. and maintained under a N2 atmosphere was added NaH (0.333 g, 8.32 mmol, 60% in mineral oil). The ice bath was removed and the solution stirred for 30 min then MeI (0.519 mL, 8.32 mmol) was added and the yellow solution stirred overnight. The reaction was diluted with H2O and extracted with Et2O. The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography (SNAP 50) eluting with hexane/EtOAc (4:1) to afford 0.660 g (28%) of (R)-tert-butyl 1-(3,4-dichlorophenyl)-3-methoxypropylcarbamate (176) as a light yellow oil.

Workup

  1. custom.cooled to 0° C.
  2. temperaturemaintained under a N2 atmosphere
  3. customThe ice bath was removed
  4. stirringthe yellow solution stirred overnight
  5. extractionextracted with Et2O
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by SiO2 chromatography (SNAP 50)
  10. washeluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-7cd0e60255b5446b92abb72c9135a34b
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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