Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylate → Ethyl 3-oxopiperidine-4-carboxylate

HRID 1053802Notes

Reaction equation

HRID 1053802 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[O:19]=[C:10]1[CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 1

HCID 419705Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylate

Product 1

HCID 3018365Ethyl 3-oxopiperidine-4-carboxylateYield 118%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate 1 (15.0 g, 50.5 mmol, 1.0 equiv) was hydrogenated in the presence of 10% Pd/C (1.5 g) catalyst under H2 at atmospheric pressure in MeOH (250 mL) for 16 h. The catalyst was filtered off and the solvent was concentrated in vacuo to give ethyl 3-oxopiperidine-4-carboxylate 2 as a light yellow solid (10.2 g, yield: 98.0%). ESI-MS (M+H)+: 172.1. 1H NMR (400 MHz, DMSO-d6) δ: 4.23 (q, 2H), 3.75 (s, 2H), 3.37 (s, 2H), 3.20-3.16 (m, 2H), 2.44 (t, 1H), 1.25 (t, 3H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-3d9816e5fc2e439a80f52eb47821c743
Source dataset
uspto-grants-2016_07
Patent number
US09394277B2

Reaction notes

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