4-[3-(Tert-butyl-dimethyl-silanyloxy)-3-methyl-but-1-ynyl]-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester → 4-[3-(Tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester

HRID 1392658Notes

Reaction equation

HRID 1392658 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[C:5]1[C:10]([C:11]#[C:12][C:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])([CH3:15])[CH3:14])=[CH:9][C:8]([C:24]2[C:29]([CH2:30][CH3:31])=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:32][CH3:33])=[N:7][C:6]=1[CH3:34])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:35])[C:5]1[C:10]([CH2:11][CH2:12][C:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])([CH3:15])[CH3:14])=[CH:9][C:8]([C:24]2[C:25]([CH2:32][CH3:33])=[CH:26][CH:27]=[CH:28][C:29]=2[CH2:30][CH3:31])=[N:7][C:6]=1[CH3:34])[CH3:2]

Participants

4

Reactant 1

HCID 669945234-[3-(Tert-butyl-dimethyl-silanyloxy)-3-methyl-but-1-ynyl]-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester

Product 1

HCID 669939814-[3-(Tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-but-1-ynyl]-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester (318 mg, 0.64 mmol) and 10% Pd/C (32 mg, 10 wt %) in MeOH (30 mL) is hydrogenated for 18 hours at 55 psi (Parr shaker). After filtering through celite, the filtrate is concentrated, and the residue purified by flash chromatography to give 4-[3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester as a colorless oil.

Workup

  1. filtrationAfter filtering through celite
  2. concentrationthe filtrate is concentrated
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-03b6ab63f4e44ac8b9a13b11b7310cd1
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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