Cesium fluoride → HCID 67812942, compound

HRID 2401424Notes

Reaction equation

HRID 2401424 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[C:19]([CH3:22])=[N:20][O:21][C:11]=3[C@H:10]([CH2:23][C:24]([O:34]C)([O:29][Si](C)(C)C)[C:25]([F:28])([F:27])[F:26])[N:9]=2)=[CH:4][CH:3]=1.[F-].[Cs+]>CO.CC(OC)(C)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[C:19]([CH3:22])=[N:20][O:21][C:11]=3[C@H:10]([CH2:23][C:24]([OH:29])([OH:34])[C:25]([F:28])([F:27])[F:26])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 25953Cesium fluorideHCID 67813201HCID 67813201, compound

Product 1

HCID 67812942HCID 67812942, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a cooled (0° C.) solution of crude (4S)-6-(4-chlorophenyl)-1-methyl-4-(3,3,3-trifluoro-2-methoxy-2-((trimethylsilyl)oxy)propyl)-4H-benzo[c]isoxazolo[4,5-e]azepine in MeOH (3 mL) was added CsF (0.048 g, 0.316 mmol). The reaction was maintained at 0° C. for 30-60 min or until complete conversion of starting material to the desired ketone/di-hydrate was observed. The reaction mixture was diluted with MTBE and aqueous 1 N HCl was added until a phase cut was observed. The aqueous phase was extracted with MTBE (3×), the combined organic phases were washed with water, dried over Na2SO4, and concentrated to give the desired product as an orange oil. The product 3-((4S)-6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepin-4-yl)-1,1,1-trifluoropropane-2,2-diol (0.121 g, 0.277 mmol, 96% yield) was used without further purification. LC/MS m/z 437 [M+H]+.

Workup

  1. additionwas added until a phase cut
  2. extractionThe aqueous phase was extracted with MTBE (3×)
  3. washthe combined organic phases were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-abd8bdd69fac4f0db719e2b061daacc9
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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