tert-butyl 4-(4-amino-3-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylate → Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylate

HRID 1503891Notes

Reaction equation

HRID 1503891 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)=[CH:4][C:3]=1[O:21][CH3:22]>[Pd].CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[O:21][CH3:22]

Participants

4

Reactant 1

HCID 68455699tert-butyl 4-(4-amino-3-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylate

Product 1

HCID 57416157Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 10% palladium on carbon (0.1 g) in methanol (30 mL) was added the product of Example 62A (0.8 g, 2.6 mmol) and the mixture was stirred at ambient temperature under hydrogen for 8 hours. The mixture was filtered and concentrated to yield the title compound. MS: 307 (M+H+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-956db23798ad4822b19b61f70d84569d
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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