Methanol → HCID 59423825, compound

HRID 501722Notes

Reaction equation

HRID 501722 reaction equation
CO.[CH2:3]([O:6][CH2:7][C@H:8]([NH:13]C(=O)C(F)(F)F)[CH2:9][CH:10]([CH3:12])[CH3:11])[CH:4]=[CH2:5].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:3]([O:6][CH2:7][C@H:8]([NH2:13])[CH2:9][CH:10]([CH3:11])[CH3:12])[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86622345HCID 86622345, compound

Product 1

HCID 59423825HCID 59423825, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step AK (3): To a mixture of methanol (90 mL) and water (10 mL), (R)-N-(1-(allyloxy)-4-methylpentan-2-yl)-2,2,2-trifluoroacetamide (1.9 g, 7.5 mmol) and potassium carbonate (3.1 g, 22.5 mmol) were added. The mixture was heated at reflux for 16 h and concentrated in vacuum to remove methanol. The mixture was poured into excess NaOH (1 M) and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuum to yield (R)-1-(allyloxy)-4-methylpentan-2-amine (1.12 g, 95%) as a colorless oil. LC-MS (M+H)+=158.07.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 16 h
  4. concentrationconcentrated in vacuum
  5. customto remove methanol
  6. additionThe mixture was poured into excess NaOH (1 M)
  7. extractionextracted with EtOAc
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-5bf0339092f94c0a9e704a7d4ca87de7
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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