Ethyl Acetate → HCID 57467658, compound

HRID 1662507Notes

Reaction equation

HRID 1662507 reaction equation
O=[O+][O-].[F:4][C:5]1[C:6]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]2([CH:28]=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:7][C:8]([O:11][CH3:12])=[N:9][CH:10]=1.[BH4-].[Na+].CCOC(C)=O>C(Cl)Cl.CO>[F:4][C:5]1[C:6]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]2([CH2:28][OH:29])[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:7][C:8]([O:11][CH3:12])=[N:9][CH:10]=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

Ozone gas was passed through a 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) at −78° C. for 10 minutes. The excess of ozone was purged off by 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, and the mixture was stirred at room temperature for 16 hours. The LCMS results indicated the reaction was completed. EtOAc (50 mL) was added, and the mixture was washed with brine (20×2 mL) and dried over Na2SO4. The solvent was removed, and the product thus obtained was good enough for use in the next step without further purification. MS ESI (pos.) m/e: 360.2 (M+H)+.

Workup

  1. customThe excess of ozone was purged off by nitrogen, and dimethylsulfide (0.3 mL)
  2. additionwas added
  3. customThe resulting reaction mixture
  4. stirringthe mixture was stirred at room temperature for 16 hours
  5. customThe LCMS results
  6. washthe mixture was washed with brine (20×2 mL)
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed
  9. customthe product thus obtained
  10. customwas good enough for use in the next step without further purification

Sources & evidence

ORD record
ord-4d13881601434535a35d0fe8c21ec7c6
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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