rel-Phenylmethyl (3R,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methoxy-1-piperidinecarboxylate → HCID 58522529, compound

HRID 81350Notes

Reaction equation

HRID 81350 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[CH2:11][C@H:10]1[O:25][CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]1[O:25][CH3:26])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58522570rel-Phenylmethyl (3R,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methoxy-1-piperidinecarboxylate

Product 1

HCID 58522529HCID 58522529, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl (3R,4R)-4-tert-butoxycarbonylamino-3-methoxy-piperidine-1-carboxylate (2.88 g) is dissolved in ethanol and combined with a spatula tip of Pd/C and hydrogenated under H2 pressure (4 bar). After 18 h the catalyst is filtered off and the solvent is eliminated in vacuo. The residue is used in the next reaction step without any further purification.

Workup

  1. filtrationAfter 18 h the catalyst is filtered off
  2. customThe residue is used in the next reaction step without any further purification

Sources & evidence

ORD record
ord-51589e2bcc7d431d84f52fe30b050afd
Source dataset
uspto-grants-2014_09
Patent number
US08846689B2

Reaction notes

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