Réaction #89767

Équation de réaction

benzyltriphenylphosphonium bromide

methyl(1S,2S)-5-oxo-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylate

sodium bis(trimethylsilyl)amide

→

methyl(1S,2S,5E)-5-benzylidene-2-[(4-phenylpiperazin-1-yl)carbonyl]-cyclohexanecarboxylate

Solvants

THF

THF

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 18 h
2. 2
   AutreThe reaction was quenched with water (20 mL)
3. 3
   Extractionextracted with EtOAc (2×)
4. 4
   LavageThe combined organic layers were washed with brine
5. 5
   Séchagedried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutreThe residue was purified by Combiflash with 20-60% EtOAc/Hex
9. 9
   Autreto give
10. 10
    Autrethe product (141 mg, 57% in yield) as well as the S.M

Mode opératoire

To a suspension of benzyltriphenylphosphonium bromide (0.397 g, 0.000880 mol) in anhydrous THF (3.0 mL) at rt was added 1.00 M of sodium bis(trimethylsilyl)amide in tetrahydrofuran (0.880 mL) dropwise. The resulting orange suspension was stirred at rt for 1 h, a solution of methyl(1S,2S)-5-oxo-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylate (202 mg, 0.000586 mol) in anhydrous THF (3.0 mL) was then added via cannula. The reaction mixture was stirred at rt for 18 h. The reaction was quenched with water (20 mL), extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by Combiflash with 20-60% EtOAc/Hex to give the product (141 mg, 57% in yield) as well as the S.M. (50 mg, 25% recovery of S.M.). MS (ESI): (M+H)+=419.2.

Source