Ethyl Acetate → HCID 57467658, compound

HRID 404393Notes

Reaction equation

HRID 404393 reaction equation
[F:1][C:2]1[C:3]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[C:20]2([CH:25]=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.O=[O+][O-].[BH4-].[Na+].CCOC(C)=O>C(Cl)Cl.CO>[F:1][C:2]1[C:3]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[C:20]2([CH2:25][OH:26])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 57467657HCID 57467657, compound

Product 1

HCID 57467658HCID 57467658, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The mixture of methyl 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(1-formylcyclopentyl)benzoate (0.13 g, 0.36 mmol) in DCM (6.0 mL) and MeOH (1.5 mL) was reacted with ozone gas at −78° C. for 10 minutes. The excess ozone was removed by flushing with nitrogen, and dimethylsulfide (0.3 mL) was added. The resulting reaction mixture was stirred at room temperature for 30 minutes. Sodium borohydride (0.13 mL, 3.6 mmol) was added to the reaction mixture, and the reaction was stirred at room temperature overnight. EtOAc (50 mL) was added, and the organic layer was washed with brine (20×2 mL) and dried over Na2SO4. After filtration, the solvent was removed. The product thus obtained was used in the next step without further purification. MS ESI (pos.) m/e: 360.2 (M+H)+.

Workup

  1. customThe excess ozone was removed
  2. customby flushing with nitrogen, and dimethylsulfide (0.3 mL)
  3. additionwas added
  4. customThe resulting reaction mixture
  5. stirringthe reaction was stirred at room temperature overnight
  6. washthe organic layer was washed with brine (20×2 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration
  9. customthe solvent was removed
  10. customThe product thus obtained
  11. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-505425f8b2524eaa924f8d57b9531ae0
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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