tert-Butylsulfinamide, (R)-(+)- → (NE,R)-2-methyl-N-[1-(5-methylsulfonylfuran-2-yl)propylidene]propane-2-sulfinamide
Reaction equation
[CH3:1][S:2]([C:5]1[O:9][C:8]([C:10](=O)[CH2:11][CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][C:15]([S@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C1COCC1.C(OCC)C.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][S:2]([C:5]1[O:9][C:8](/[C:10](=[N:20]/[S@@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])/[CH2:11][CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3]Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Procedure
To a solution of 1-(5-methanesulfonyl-furan-2-yl)-propan-1-one (1.1 g, 5.5 mmol) in THF (30 mL) was added (R)-(+)-2-methyl-2-propanesulfinamide (0.750 g, 6.06 mmol) and titanium (IV) isopropoxide (6 mL, 25 mmol) and the mixture was warmed at reflux. After 18 hours, the mixture was cooled to room temperature, and diluted with diethyl ether (100 mL) and water (6 mL). The mixture was stirred for 10 minutes, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of 0-80% EtOAc-hexanes to afford (R)-2-methyl-propane-2-sulfinic acid[1-(5-methanesulfonyl-furan-2-yl)-prop-(E)-ylidene]-amide.
Workup
- temperaturethe mixture was warmed
- temperatureat reflux
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by silica gel chromatography
- washeluting with a gradient of 0-80% EtOAc-hexanes
Sources & evidence
- ORD record
- ord-f9ef314eb1ab4cabb92f4afe78d798ec
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338610B2
Reaction notes
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