Hydrochloric Acid → HCID 10902032, compound

HRID 1374419Notes

Reaction equation

HRID 1374419 reaction equation
O[CH:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])[C@H:5]([CH3:14])[CH2:4][CH:3]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].CS(Cl)(=O)=O.C(N(CC)CC)C.Cl>ClCCl>[CH3:14][C@@H:5]1[CH2:4][C:3]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[CH:2][CH2:7][N:6]1[C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11822675HCID 11822675, compound

Product 1

HCID 10902032HCID 10902032, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-allyl 4-tert-butyl (2R)-5-hydroxy-2-methyl-1,4-piperidinedicarboxylate (1.85 g, 6.2 mmol) in dichloromethane (40 ml) were added at −30° C. methanesulfonyl chloride and triethylamine, and the mixture was stirred 0° C. for 2 hours. The reaction mixture was poured into diluted hydrochloric-acid and the mixture was extracted three times with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was dissolved in a mixture of toluene (5 ml) and dichloromethane (10 ml). The solution was cooled to 0° C. and thereto was added DBU. The mixture was stirred for 1 hour. The reaction mixture was poured into diluted hydrochloric acid and extracted three times with ethyl acetate. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel (30 g) chromatography to give 1-allyl 4-tert-butyl (2R)-2-methyl-3,6-dihydro-1,4(2 H)-pyridinedicarboxylate (1.33 g, 76%).

Workup

  1. extractionthe mixture was extracted three times with chloroform
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in a mixture of toluene (5 ml) and dichloromethane (10 ml)
  6. temperatureThe solution was cooled to 0° C.
  7. additionwas added DBU
  8. stirringThe mixture was stirred for 1 hour
  9. additionThe reaction mixture was poured into diluted hydrochloric acid
  10. extractionextracted three times with ethyl acetate
  11. washThe organic layer was washed with water
  12. dry with materiala saturated aqueous sodium chloride solution, and dried over magnesium sulfate
  13. customThe solvent was removed under reduced pressure
  14. customthe residue was purified by silica gel (30 g) chromatography

Sources & evidence

ORD record
ord-6591bc92aac54453baa62572fb461089
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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