6-(2-tert-Butoxycarbonyl-vinyl)-pyridine-2-carboxylic acid methyl ester → 6-(2-tert-Butoxycarbonyl-ethyl)-piperidine-2-carboxylic acid methyl ester

HRID 2354864Notes

Reaction equation

HRID 2354864 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[CH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:6]=1)=[O:4]>C(O)(=O)C.O=[Pt]=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:6]1)=[O:4]

Participants

4

Reactant 1

HCID 668421646-(2-tert-Butoxycarbonyl-vinyl)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 668423056-(2-tert-Butoxycarbonyl-ethyl)-piperidine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Compound 2 (1.0 g) is dissolved in glacial acetic acid (10 ml) and PtO2 (100 mg) is added. Hydrogenation is carried out in Parr shaker at 55 psi for 3 days. The catalyst is removed by filtration through Celite, and the solvent is evaporated to give the desired product as a yellow oil. 1H NMR (CD3OD) δ 3.73 (s, 3H), 3.40-3.33 (m, 1H), 2.61-2.52 (m, 1H), 2.34-2.29 (m, 2H), 2.03-1.99 (m, 1H), 1.93-1.88 (m, 1H), 1.76-1.68 (m, 3H), 1.50-1.33 (m, 11H), 1.11-1.02 (m, 1H).

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-77fef2e97094401c9d572dca9b06c2cf
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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