Tetrahydrofuran → N-[2-[4-[4-formylphenyl]-3-cyclohexen-1-yl]-propyl] 2-propanesulfonamide
Reaction equation
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][CH:10]([CH:13]([CH3:22])[CH2:14][NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])[CH2:9][CH:8]=1)(=O)=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:35]1[CH:40]=[CH:39][C:38](N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=[CH:37][CH:36]=1.C1C[O:59][CH2:58]C1>>[CH:58]([C:38]1[CH:39]=[CH:40][C:35]([C:7]2[CH2:12][CH2:11][CH:10]([CH:13]([CH3:22])[CH2:14][NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])[CH2:9][CH:8]=2)=[CH:36][CH:37]=1)=[O:59]Participants
Procedure
N-[2-[4-[[(trifluoromethyl)sulfonyl]oxy]-3-cyclohexen-1-yl]propyl] 2-propanesulfonamide: To a −78° C. solution of 1.0 g (3.82 mmol) of the material prepared in Preparation 2 in 6 ml of THF was added 8.4 ml of a 1 M solution of lithium bis(trimethylsilyl)amide in THF (8.4 mmol). The bath was removed and the mixture was stirred for 30 min and then 1.46 g (4.09 mmol) of N-phenyltrifluoromethane sulfonimide was added at ambient temperature. The mixture was stirred for 24 h. The reaction was quenched with NH4Cl saturated solution and extracted three times with ethyl acetate. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (125 g of silica gel, 15% ethyl acetate/hexane) of the residue afforded 395 mg (26%) of the title compound.
Workup
- customThe bath was removed
- stirringThe mixture was stirred for 24 h
- customThe reaction was quenched with NH4Cl saturated solution
- extractionextracted three times with ethyl acetate
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-fb7757cd6818401497f915bffbb7bdfa
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362230B1
Reaction notes
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