HCID 68513323, compound → HCID 68512476, compound

HRID 1716561Notes

Reaction equation

HRID 1716561 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[N+:22]([O-])=O)[C@H:10]([OH:25])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C(O)C.[Pd]>[C:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[NH2:22])[C@H:10]([OH:25])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 68513323HCID 68513323, compound

Product 1

HCID 68512476HCID 68512476, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of racemic 1-Boc-trans-3-hydroxy-4-(4-methyl-2-nitro-phenylamino)-piperidine (15.0 g, 42.6 mmol) and 10% Pd on carbon (1.5 g, 10% by weight) in ethanol (280 mL) was stirred under 1 atm of H2 gas for 17 h. The solid catalyst was then removed by filtration through Celite and all volatiles were removed under reduced pressure to yield the product, racemic 1-Boc-trans-4-(2-amino-4-methyl-phenylamino)-3-hydroxy-piperidine as a heavy oil (14.1 g, quant).

Workup

  1. customThe solid catalyst was then removed by filtration through Celite
  2. customall volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-b0543fa382ed49fc9d0f490b76646dba
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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