t-Butyl 5-(6-hydroxymethylpyridin-2-yl)pent-4-ynoate → t-Butyl 5-(6-hydroxymethylpyridin-2-yl)pentanoate

HRID 1668537Notes

Reaction equation

HRID 1668537 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]#[C:10][CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:5][CH:4]=1>[Pt](=O)=O.CCO>[OH:1][CH2:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 58105203t-Butyl 5-(6-hydroxymethylpyridin-2-yl)pent-4-ynoate

Product 1

HCID 58105232t-Butyl 5-(6-hydroxymethylpyridin-2-yl)pentanoateYield 99.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a 200 mL round-bottom flask, 2.76 g of t-butyl 5-(6-hydroxymethylpyridin-2-yl)pent-4-ynoate, 50 mg of platinum dioxide and 25 mL of EtOH were added, the mixture was stirred under hydrogen atmosphere at room temperature for 8 hours. The insoluble material was removed off, and then the filtrate was concentrated to give 2.78 g of t-butyl 5-(6-hydroxymethylpyridin-2-yl)pentanoate as a yellow oil.

Workup

  1. customThe insoluble material was removed off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-59aa189e8989448fa249c667e3d29834
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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