tert-Butyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate → tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

HRID 1469235Notes

Reaction equation

HRID 1469235 reaction equation
[OH:1][C:2]1([CH2:15][N+:16]([O-])=O)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:16][CH2:15][C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 53486300tert-Butyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate

Product 1

HCID 23396319tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate (20.42 g, 78.4 mmol) and 20% palladium hydroxide on carbon (1.21 g) in ethanol (250 mL) was hydrogenated at 40 psi (2.8×105 Pa) for 3 d on a Parr apparatus. More 20% palladium hydroxide on carbon (1.0 g) was added and the hydrogenation was continued for 2 more days. The mixture was filtered through CELITE filter agent and the filtrate was concentrated to provide tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate, which was concentrated from toluene (200 mL) to remove residual ethanol before use in the next reaction.

Workup

  1. filtrationThe mixture was filtered through CELITE
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4ee5d452ce334a7a9b7212564aaf55df
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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