Triethylamine → 5-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-pentanoic acid butyl ester

HRID 860054Notes

Reaction equation

HRID 860054 reaction equation
[CH2:1]([O:5][C:6](=[O:27])[CH2:7][CH2:8][C:9]#[C:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:12]=1)[CH2:2][CH2:3][CH3:4].CCN(CC)CC.[H][H]>CCO.O=[Pt]=O>[CH2:1]([O:5][C:6](=[O:27])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 696660335-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-pent-4-ynoic acid butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 696665415-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-pentanoic acid butyl esterYield 94.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-5 (6.54 g, 17.8 mmol), Et3N (1.85 mL, 13.3 mmol), and PtO2 (0.405 g, 1.78) in EtOH (150 mL) was stirred under a balloon of hydrogen for 6 h. Filtration through celite and evaporative removal of the solvent afforded 6.23 g of 6-6 as a colorless oil. The crude product was used directly in the next step without purification.

Workup

  1. filtrationFiltration through celite
  2. customremoval of the solvent

Sources & evidence

ORD record
ord-26240f8d8a25487a9dcb69b83d72ba7d
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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