Tert-butyl 4-(3-nitrophenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate → tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate

HRID 347722Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 1,2,3,6-tetrahydro-4-(3-nitrophenyl)pyridine-1-carboxylic acid tert-butyl ester (1.7 g), which is prepared according to the method disclosed in Synthesis, 993 (1991), in ethanol (100 ml) is added 10% palladium on carbon (wet, 1.7 g), and the mixture is stirred at 25° C. under hydrogen atmosphere for 5 hours. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient, 0% to 100% ethyl acetate/hexane) to give the title compound (1.1 g).

Workup

customThe catalyst is removed by filtration
concentrationthe filtrate is concentrated under reduced pressure
customThe residue is purified by silica gel column chromatography (eluent: gradient, 0% to 100% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-5d5f8207c71b4be2a90f322700c58051
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176199B2

Reaction notes

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