Triethylamine → (R)-2-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane
Reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:10]=[CH:11][C:12]([O:27][CH3:28])=[C:13]([C:15]([CH3:26])([CH3:25])[CH2:16][C@@:17]([C:21]([F:24])([F:23])[F:22])([OH:20])[CH2:18]O)[CH:14]=1.CS(Cl)(=O)=O>C(Cl)Cl>[F:8][C:9]1[CH:10]=[CH:11][C:12]([O:27][CH3:28])=[C:13]([C:15]([CH3:26])([CH3:25])[CH2:16][C@:17]2([C:21]([F:24])([F:23])[F:22])[CH2:18][O:20]2)[CH:14]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Triethylamine (8.2 mL, 58.8 mmol) was added to a solution of (2R)-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-(trifluoromethyl)-1,2-pentanediol (3.4 g, 10.9 mmol) in DCM (34 mL). This solution was then cooled to 0° C. and neat methanesulphonyl chloride (1.1 mL, 15.3 mmol) was added over 5 min keeping the temperature at 0-5° C. The resulting suspension was stirred at 0-5° C. for 15 min before warming to 20° C. The reaction mixture was then left to stir overnight. Further neat methanesulphonyl chloride (0.84 μL, 0.1 eq) was added at room temperature and the mixture stirred for 15 min. The reaction mixture was then washed successively with 1M HCl (3×12 mL), 9% aqueous sodium bicarbonate (12 mL) and water (12 mL) before evaporating to dryness to afford the title compound, 3.08 g.
Workup
- customat 0-5° C
- temperaturebefore warming to 20° C
- waitThe reaction mixture was then left
- stirringto stir overnight
- stirringthe mixture stirred for 15 min
- washThe reaction mixture was then washed successively with 1M HCl (3×12 mL), 9% aqueous sodium bicarbonate (12 mL) and water (12 mL)
- custombefore evaporating to dryness
Sources & evidence
- ORD record
- ord-5ff5562be53a47cdb9f440bee083dac4
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943651B2
Reaction notes
Loading…