Ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylate → Ethyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

HRID 44689

Reaction equation

HRID 44689 reaction equation
[OH:1][C:2]1([CH2:13][N+:14]([O-])=O)[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:14][CH2:13][C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 22708806Ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylate

Product 1

HCID 14049029Ethyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate (5.2 g, 22.4 mmol) and 20% palladium hydroxide on carbon (0.50 g) in ethanol (190 mL) was hydrogenated at 35 psi (2.4×105 Pa) on a Parr apparatus for 5 h. The mixture was filtered through CELITE filter agent and the filtrate was concentrated. By 1H NMR analysis, the reaction was incomplete and the crude material was subjected to the reaction conditions again with fresh 20% palladium hydroxide on carbon (0.50 g) for another 24 h. The mixture was filtered through CELITE filter agent and the filtrate was concentrated to provide ethyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate, which was concentrated from chloroform to remove residual ethanol before using in the next reaction.

Workup

  1. filtrationThe mixture was filtered through CELITE
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated
  4. customthe crude material was subjected to the reaction conditions again with fresh 20% palladium hydroxide on carbon (0.50 g) for another 24 h
  5. filtrationThe mixture was filtered through CELITE
  6. filtrationfilter agent
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e97a7697d026407fb91118f4daf04744
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Linked notes

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