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

HRID 535097

Reaktionsgleichung

Reaktionsgleichung von HRID 535097
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ea4f5bccb6634db994c23d91c1e84e6e
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853243B2

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