反応 #89767

反応方程式

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

溶媒

THF

THF

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 18 h
2. 2
   その他The reaction was quenched with water (20 mL)
3. 3
   抽出extracted with EtOAc (2×)
4. 4
   洗浄The combined organic layers were washed with brine
5. 5
   乾燥dried over sodium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The residue was purified by Combiflash with 20-60% EtOAc/Hex
9. 9
   その他to give
10. 10
    その他the product (141 mg, 57% in yield) as well as the S.M

実験手順

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.

出典