Water → (1S,2R)-4,4-Difluoro-1-(1-methyl-1H-pyrazol-5-yl)cyclohexane-1,2-diol
Reaction equation
CS(N)(=O)=O.[OH2:6].[F:7][C:8]1([F:20])[CH2:13][CH2:12][C:11]([C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)=[CH:10][CH2:9]1.S([O-])([O-])=[O:22].[Na+].[Na+]>C(O)(C)(C)C>[F:20][C:8]1([F:7])[CH2:13][CH2:12][C@@:11]([C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)([OH:6])[C@H:10]([OH:22])[CH2:9]1Participants
Procedure
To a solution of methanesulfonamide (480 mg, 5.05 mmol) in a mixed solvent of t-butanol (10 mL) and water (10 mL), AD-mixα (Sigma-Aldrich Corp.; 7.10 g) was added, and the reaction solution was stirred at room temperature for 10 minutes. To the reaction solution, a solution of the 5-(4,4-difluorocyclohex-1-en-1-yl)-1-methyl-1H-pyrazole (1.0 g, 5.05 mmol) prepared in Example 47a in t-butanol (5 mL) was added with cooling on ice, and the reaction solution was vigorously stirred at room temperature for 16 hours. To the reaction solution, an aqueous sodium sulfite solution (10 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate to yield the title compound in a crude form.
Workup
- temperaturewith cooling on ice
- stirringthe reaction solution was vigorously stirred at room temperature for 16 hours
- extractionfollowed by extraction with ethyl acetate (50 mL)
- dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
Sources & evidence
- ORD record
- ord-69e30341ae9145f7a629bcb79bd7f0b6
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889741B2
Reaction notes
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