2-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-methoxypiperidine-2,3-dicarboxylate → (2s,3s,5s)-5-Methoxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid

HRID 61472Notes

Reaction equation

HRID 61472 reaction equation
C([N:8]1[CH2:13][C@@H:12]([O:14][CH3:15])[CH2:11][C@H:10]([C:16]([O:18][CH3:19])=[O:17])[C@H:9]1[C:20]([O:22]CC1C=CC=CC=1)=[O:21])C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:15][O:14][C@@H:12]1[CH2:13][NH:8][C@H:9]([C:20]([OH:22])=[O:21])[C@@H:10]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]1

Participants

5

Reactant 2

HCID 1317319302-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-methoxypiperidine-2,3-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67305316(2s,3s,5s)-5-Methoxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-benzyl 3-methyl(2S,3S,5S)-1-benzyl-5-methoxypiperidine-2,3-dicarboxylate (30.0 mg, 0.0000755 mol) in 2 mL of MeOH was hydrogenated in the presence of 10% Pd/C, under a balloon pressure of hydrogen, for 1 h. The catalyst was filtered off and the filtration was concentrated to dry. The residue was used directly in next step (16 mg, 97.6%). MS (ESI): (M+H)+=218.0.

Workup

  1. filtrationThe catalyst was filtered off
  2. filtrationthe filtration
  3. concentrationwas concentrated
  4. customto dry

Sources & evidence

ORD record
ord-cdbe5102ea3a48bba1fc3d6e5b6e4225
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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