Sodium bis(trimethylsilyl)amide → Methyl (1s,2s,5e)-5-benzylidene-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylate

HRID 61489

反応式

HRID 61489 の反応式
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O=[C:39]1[CH2:44][C@H:43]([C:45]([O:47][CH3:48])=[O:46])[C@@H:42]([C:49]([N:51]2[CH2:56][CH2:55][N:54]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[CH2:53][CH2:52]2)=[O:50])[CH2:41][CH2:40]1>C1COCC1>[CH:2](=[C:39]1/[CH2:40][CH2:41][C@H:42]([C:49]([N:51]2[CH2:56][CH2:55][N:54]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[CH2:53][CH2:52]2)=[O:50])[C@@H:43]([C:45]([O:47][CH3:48])=[O:46])[CH2:44]/1)/[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 2734970Benzyltriphenylphosphonium bromideHCID 67304345Methyl (1s,2s)-5-oxo-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylate

生成物 1

HCID 67304520Methyl (1s,2s,5e)-5-benzylidene-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

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.

後処理

  1. stirringThe reaction mixture was stirred at rt for 18 h
  2. customThe reaction was quenched with water (20 mL)
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by Combiflash with 20-60% EtOAc/Hex
  9. customto give
  10. customthe product (141 mg, 57% in yield) as well as the S.M

出典と根拠

ORDレコード
ord-b70ab8e192c445b3968a739d462c372e
出典データセット
uspto-grants-2016_09
特許番号
US09440958B2

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