2-benzyl 3-methyl (2S,3S,5R)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate → (2S,3S,5R)-5-hydroxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid

HRID 535050Notes

Reaction equation

HRID 535050 reaction equation
C([N:8]1[CH2:13][C@H:12]([OH:14])[CH2:11][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[C@H:9]1[C:19]([O:21]CC1C=CC=CC=1)=[O:20])C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:14][C@H:12]1[CH2:13][NH:8][C@H:9]([C:19]([OH:21])=[O:20])[C@@H:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]1

Participants

5

Reactant 2

HCID 1317319262-benzyl 3-methyl (2S,3S,5R)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67305204(2S,3S,5R)-5-hydroxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  1. filtrationAfter filtered off the catalyst
  2. filtrationthe filtration
  3. concentrationwas concentrated
  4. customto dry in vacuo

Sources & evidence

ORD record
ord-429d373a67c84012a56908ca36be63c7
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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