Reaktion #89719

ord-69b8dd9ebd4a4df0b81f36ab3f66cfaf

Reaktionsgleichung

[H][H]
hydrogen
COC(=O)[C@H]1C[C@@H](O)CN(Cc2ccccc2)[C@@H]1C(=O)OCc1ccccc1
2-benzyl 3-methyl(2S,3S,5R)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate
→
COC(=O)[C@H]1C[C@@H](O)CN[C@@H]1C(=O)O
(2S,3S,5R)-5-hydroxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid

Edukte

[H][H]
hydrogen
COC(=O)[C@H]1C[C@@H](O)CN(Cc2ccccc2)[C@@H]1C(=O)OCc1ccccc1
2-benzyl 3-methyl(2S,3S,5R)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate

Reagenzien

[Pd]
Pd/C

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationAfter filtered off the catalyst
  2. 2
    Filtrationthe filtration
  3. 3
    Einengenwas concentrated
  4. 4
    Sonstigeto dry in vacuo

Vorschrift

A mixture of 2-benzyl 3-methyl(2S,3S,5R)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate (1.00 g, 0.00261 mol) in 10 mL of methanol was hydrogenated in the presence of 10% Pd/C, under a balloon pressure of hydrogen, for 3 h. After filtered off the catalyst, the filtration was concentrated to dry in vacuo and used directly in next step. MS (ESI): (M+H)+=204.0.

Quelle

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