Water → HCID 67598444, compound
Reaction equation
[CH3:1][NH:2][S:3]([CH3:6])(=[O:5])=[O:4].[H-].[Na+].[F:9][C:10]([F:29])([F:28])[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[O:21][C:20]([CH3:26])([CH3:25])[C@@H:19]1[O:27][C@H:18]21.O>CS(C)=O>[OH:27][C@@H:19]1[C@@H:18]([CH2:6][S:3]([NH:2][CH3:1])(=[O:5])=[O:4])[C:17]2[C:22](=[CH:23][CH:24]=[C:15]([O:14][CH2:13][CH2:12][CH2:11][C:10]([F:29])([F:9])[F:28])[CH:16]=2)[O:21][C:20]1([CH3:26])[CH3:25]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Under argon, 0.77 g (7.1 mmol) of N-methyl-methanesulfonamide was added to a suspension of 0.065 g (2.7 mmol) of 80 percent sodium hydride in 3 ml of DMSO, and the mixture was stirred at RT for 20 min. 1.65 g (5.5 mmol) of (3R,4R)-(+)-6-(4,4,4-trifluorobutoxy)-2,2-dimethyl-3,4-epoxychroman, dissolved in 5 ml of DMSO, were then added dropwise and the batch was left to stand at RT for 4 days and then heated at 45° C. for a further 9 h. The mixture was subsequently poured into water and the precipitate was filtered off with suction and dried thoroughly under reduced pressure, giving 1.9 g of (3R,4S)-(+)-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)chroman-4-yl]-N-methyl-methanesulfonamide, which was recrystallized from a little isopropanol (->1.4 g; m.p. 178-179° C.; optical purity (chiral HPLC) 100%).
Workup
- additionwere then added dropwise
- waitthe batch was left
- waitto stand at RT for 4 days
- temperatureheated at 45° C. for a further 9 h
- filtrationthe precipitate was filtered off with suction
- customdried thoroughly under reduced pressure
Sources & evidence
- ORD record
- ord-860cb93b231848d2a57af261041ef14e
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06008245
Reaction notes
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