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

HRID 535097

반응식

HRID 535097 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ea4f5bccb6634db994c23d91c1e84e6e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853243B2

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