Benzyl Alcohol → HCID 131737221, compound

HRID 64446Notes

Reaction equation

HRID 64446 reaction equation
[CH3:1][C:2]1([CH3:17])[O:7][CH2:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)(C([O-])=O)[CH2:4][O:3]1.[Na+].Cl[C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21].[N-:27]=[N+]=[N-].[Na+].[CH2:31](O)[C:32]1[CH:37]=CC=CC=1>O1CCOCC1.O.C(OCC)C>[CH2:23]([O:22][C:20](=[O:21])[NH:27][C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:4][O:3][C:2]([CH3:1])([CH3:17])[O:7][CH2:6]1)[C:24]1[CH:26]=[CH:37][CH:32]=[CH:31][CH:25]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 33557Sodium AzideHCID 62365Isobutyl chloroformateHCID 90072617HCID 90072617, compound

Product 1

HCID 131737221HCID 131737221, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 340 mg of sodium 2,2-dimethyl-5-(pyridin-2-yl)-1,3-dioxane-5-carboxylate in 5 ml of dioxane and 1 ml of water was added 0.21 ml of isobutyl chloroformate under ice-cooling, followed by stirring for 1 hour. A solution of 850 mg of sodium azide in 3 ml of water was added thereto, followed by stirring for 10 minutes under ice-cooling. To the reaction mixture were added water and diethyl ether to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the obtained residue was added 5 ml of toluene, followed by stirring at 100° C. for 5 minutes. After leaving to be cooled, 0.7 ml of benzyl alcohol was added thereto at room temperature, followed by stirring at 100° C. for 19 hours. After leaving to be cooled, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 223 mg of benzyl[2,2-dimethyl-5-(pyridin-2-yl)-1,3-dioxan-5-yl]carbamate.

Workup

  1. temperaturecooling
  2. stirringby stirring for 10 minutes under ice-
  3. temperaturecooling
  4. customa layer separation operation
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. additionTo the obtained residue was added 5 ml of toluene
  9. stirringby stirring at 100° C. for 5 minutes
  10. customAfter leaving
  11. temperatureto be cooled
  12. customat room temperature
  13. stirringby stirring at 100° C. for 19 hours
  14. customAfter leaving
  15. temperatureto be cooled
  16. customthe solvent was evaporated under reduced pressure
  17. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9771d34602b24f909cfe21c6ab6115a5
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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