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Ethyl trans-4-azido-3-methoxy-1-piperidinecarboxylate → Ethyl trans-4-amino-3-methoxy-1-piperidinecarboxylate

HRID 981298
Notes
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Reaction equation

HRID 981298 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][C@H:5]1[O:15][CH3:16])=[N+]=[N-].[H][H]>[Pd].CO>[NH2:1][C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][C@H:5]1[O:15][CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 13677848Ethyl trans-4-azido-3-methoxy-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 13677747Ethyl trans-4-amino-3-methoxy-1-piperidinecarboxylateYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 15.6 parts of ethyl trans-4-azido-3-methoxy-1-piperidinecarboxylate and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated in vacuo, yielding 13.8 parts (97.4%) of ethyl trans-4-amino-3-methoxy-1-piperidinecarboxylate as a residue (interm. 5).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-afed1b3cc59e414a9f5917e0bd69902c
Source dataset
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04990521

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes