tert-butyl-4-(4-aminonaphthalen-1-yl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(4-aminonaphthalen-1-yl)piperidine-1-carboxylate

HRID 2093801Notes

Reaction equation

HRID 2093801 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([NH2:24])=[CH:16][CH:15]=2)=[CH:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([NH2:24])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67168077tert-butyl-4-(4-aminonaphthalen-1-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 58257106Tert-butyl 4-(4-aminonaphthalen-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl-4-(4-aminonaphthalen-1-yl)-5,6-dihydropyridine-1(2H)-carboxylate in 50 mL of MeOH was added 10 wt % Pd—C (100 mg). The reaction was degassed to remove air and stirred under 1 atm. H2 until the starting material is consumed. The Pd—C was removed by filtration and the resulting solution was concentrated in vacuo to afford tert-butyl-4-(4-aminonaphthalen-1-yl)piperidine-1-carboxylate.

Workup

  1. customThe reaction was degassed
  2. customto remove air
  3. customH2 until the starting material is consumed
  4. customThe Pd—C was removed by filtration
  5. concentrationthe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-86165473068b41f7bc7faf6cc45585ac
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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