HCID 118308679, compound → HCID 118308711, compound

HRID 923474Notes

Reaction equation

HRID 923474 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N+:16]([O-])=O)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]2)=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH2:16])[CH2:9][O:10][C:11]([CH3:14])([CH3:15])[O:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 118308679HCID 118308679, compound

Product 1

HCID 118308711HCID 118308711, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 490 mg of 5-(4-fluorophenyl)-2,2-dimethyl-5-nitro-1,3-dioxane in 7.4 ml of acetic acid was added 628 mg of zinc powder, followed by stirring at room temperature for 2 hours. The insoluble materials were separated by filtration and washed with chloroform, and the filtrate was then concentrated under reduced pressure. To the obtained residue was added a 1 M aqueous sodium hydroxide solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 325 mg of 5-(4-fluorophenyl)-2,2-dimethyl-1,3-dioxan-5-amine.

Workup

  1. customThe insoluble materials were separated by filtration
  2. washwashed with chloroform
  3. concentrationthe filtrate was then concentrated under reduced pressure
  4. additionTo the obtained residue was added a 1 M aqueous sodium hydroxide solution
  5. extractionfollowed by extraction with chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was then evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a9db5762336848e192177d7e8eacb56b
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

Loading…