Methanol → HCID 18670568, compound

HRID 1059316Notes

Reaction equation

HRID 1059316 reaction equation
ClC(O[CH:5](Cl)[CH3:6])=O.[CH3:8]O.C([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])C.[C:17](OC([O-])=O)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>ClC(Cl)C>[C:20]([O:19][C:17]([N:12]1[CH2:13][CH2:14][C:5](=[CH2:6])[CH2:8][CH:15]1[CH3:16])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 5213051-Chloroethyl chloroformateHCID 22064466Tert-butyldicarbonate

Product 1

HCID 18670568HCID 18670568, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

6.41 g of 1-benzyl-2-methyl-4-methylenepiperidone was dissolved in 70 ml of dichloroethane and 5.92 g of 1-chloroethyl chloroformate was added thereto under ice-cooling. After heating the mixture under reflux for 50 minutes, 100 ml of methanol was added thereto and the resulting mixture was allowed to stand at room temperature overnight. Then triethylamine was added to the reaction mixture under ice-cooling until the pH value reached 9. Further, 7.64 g of tert-butyl dicarbonate was added thereto and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed successively with water, 1 N hydrochloric acid, a saturated aqueous solution of sodium chloride and a saturated aqueous solution of sodium bicarbonate and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 7.2 g of the title compound as a colorless oily substance.

Workup

  1. temperatureunder ice-cooling
  2. temperatureAfter heating the mixture
  3. temperatureunder reflux for 50 minutes
  4. temperaturecooling until the pH value
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additiondiluted with ethyl acetate
  7. washwashed successively with water, 1 N hydrochloric acid
  8. dry with materiala saturated aqueous solution of sodium chloride and a saturated aqueous solution of sodium bicarbonate and dried over anhydrous magnesium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3086a28003dd402dba1278d202bd529d
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…