Reaktion #89748

ord-7066d252805340cab58e3e975c3a037e

Reaktionsgleichung

C=CCOC(=O)O[C@H]1C[C@H](C(=O)OC)[C@@H](C(=O)N2CCN(c3ccccc3)CC2)N(C(=O)OC)C1
dimethyl(2S,3S,5S)-5-[(allyloxy)carbonyl]oxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate
C1CCOC1
tetrahydrofuran
→
C=CCO[C@H]1C[C@H](C(=O)OC)[C@@H](C(=O)N2CCN(c3ccccc3)CC2)N(C(=O)OC)C1
dimethyl(2S,3S,5S)-5-(allyloxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Edukte

C=CCOC(=O)O[C@H]1C[C@H](C(=O)OC)[C@@H](C(=O)N2CCN(c3ccccc3)CC2)N(C(=O)OC)C1
dimethyl(2S,3S,5S)-5-[(allyloxy)carbonyl]oxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate
C1CCOC1
tetrahydrofuran

Reagenzien

[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1
tetrakis(triphenylphosphine)palladium(O)

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwas refluxed for 2 h
  2. 2
    EinengenThe mixture was concentrated
  3. 3
    Sonstigeto dry

Vorschrift

A mixture of dimethyl(2S,3S,5S)-5-[(allyloxy)carbonyl]oxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate (100 mg, 0.0002 mol) and tetrakis(triphenylphosphine)palladium(O) (24 mg, 0.000020 mol) in tetrahydrofuran (5.00 mL, 0.0616 mol) was refluxed for 2 h. The mixture was concentrated to dry and used directly in next step.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09440958B2uspto-grants-2016_09