Phenyl triflimide → N-[2-[4-oxocyclohexyl]ethyl] 2-propanesulfonamide

HRID 566474Notes

Reaction equation

HRID 566474 reaction equation
FC(F)(F)S([O:6][C:7]1[CH2:12][CH2:11][CH:10]([CH:13](C)[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+].C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1>C1COCC1>[O:6]=[C:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 142176Phenyl triflimideHCID 2733832Lithium HexamethyldisilazideHCID 15541825HCID 15541825, compound

Product 1

HCID 22624691N-[2-[4-oxocyclohexyl]ethyl] 2-propanesulfonamideYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. customThe bath was removed
  2. stirringThe mixture was stirred for 24 h
  3. customThe reaction was quenched with NH4Cl saturated solution
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea5e78b645794ea699c8001743a83ffa
Source dataset
uspto-grants-2001_01
Patent number
US06174922B1

Reaction notes

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