1-tert-Butyl 4-ethyl 4-(prop-2-en-1-yl)piperidine-1,4-dicarboxylate → HCID 46318390, compound

HRID 1777342Notes

Reaction equation

HRID 1777342 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH:20]=[CH2:21])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][CH3:21])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 162182701-tert-Butyl 4-ethyl 4-(prop-2-en-1-yl)piperidine-1,4-dicarboxylate

Product 1

HCID 46318390HCID 46318390, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5% Pd/C (0.6 g, 50% wet) is added to a stirred solution of 4-allylpiperidine-1,4-dicarboxylicacid-1-tert-butylester-4-ethyl ester (2.1 g, 0.007 mol) in ethanol (20 mL). Hydrogen gas is bubbled through the reaction mixture at room temperature for 20 minutes. Reaction mixture is filtered through celite bed and washed with methanol (3×5 mL). Combined filtrate is concentrated under reduced pressure to give 4-propylpiperidine-1,4-dicarboxylic acid-1-tert-butyl ester-4-ethyl ester.

Workup

  1. customHydrogen gas is bubbled through the reaction mixture at room temperature for 20 minutes
  2. customReaction mixture
  3. filtrationis filtered through celite bed
  4. washwashed with methanol (3×5 mL)
  5. concentrationCombined filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-485f0d9d67e143d3830aa9515d0b0795
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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