Sodium Bicarbonate → HCID 69663791, compound

HRID 1245334Notes

Reaction equation

HRID 1245334 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[O:16][C:17]1[CH:29]=[CH:28][C:20]2[C:21]([C:24]([F:27])([F:26])[F:25])=[N:22][O:23][C:19]=2[C:18]=1[CH2:30][CH2:31][CH3:32])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[OH:8][CH2:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[O:16][C:17]1[CH:29]=[CH:28][C:20]2[C:21]([C:24]([F:27])([F:26])[F:25])=[N:22][O:23][C:19]=2[C:18]=1[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 69663671HCID 69663671, compound

Product 1

HCID 69663791HCID 69663791, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-{[(1S,2S)-2-({[tert-butyl(dimethyl)silyl]oxy}-methyl)cyclohexyl]oxy}-7-propyl-3-(trifluoromethyl)-1,2-benzisoxazole (550 mg, 1.17 mmol), from this Example step 2, in dry THF (17 ml) was added tetrabutylammonium fluoride (1M THF, 1.75 mL, 1.75 mmol) at 0° C. The reaction mixture was stirred at room temperature for two hours. Saturated NaHCO3 was added. The mixture was extracted with ethyl acetate three times and the combined organic layers washed with brine, dried over Na2CO3 and filtered. The solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel using ethyl acetate and hexane (20:80) to give the title compound.

Workup

  1. customat 0° C
  2. extractionThe mixture was extracted with ethyl acetate three times
  3. washthe combined organic layers washed with brine
  4. dry with materialdried over Na2CO3
  5. filtrationfiltered
  6. customThe solvent was evaporated in vacuo
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4d19c6df61aa4064af3575496d2d84bb
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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