tert-butyl 4-[3-(ethoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-[3-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate

HRID 385292Notes

Reaction equation

HRID 385292 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]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[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]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 57880536tert-butyl 4-[3-(ethoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 57880576Tert-butyl 4-[3-(ethoxycarbonyl)phenyl]piperidine-1-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(3-ethoxycarbonyl-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (11.28 g, 34.035 mmol) in ethanol (680 mL) was pumped through Pd/C cartridge using H-Cube apparatus (20° C., 10 bar, 2 mL/min.). The solvent was then evaporated under reduced pressure to give 4-(3-ethoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (10.55 g, 93%), which can be used in the next step without further purification. 1H-NMR (400 MHz, CDCl3): δ=1.39-1.43 (t, 3H), 1.51 (s, 9H), 1.61-1.72 (dq, 1H), 1.78-1.90 (m, 1H), 2.66-2.74 (dt, 1H), 2.74-2.89 (m, 1H), 4.20-4.31 (m, 1H), 4.32-4.42 (q, 2H), 7.39-7.41 (m, 2H), 7.88-7.92 (m, 2H). MS: m/z=334 (M+1).

Workup

  1. customapparatus (20° C., 10 bar, 2 mL/min.)
  2. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-63fb22282dfc423891d5b2be7e7305fb
Source dataset
uspto-grants-2013_02
Patent number
US08367844B2

Reaction notes

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