Methyl 2,2-dimethyl-4-[3-(3-pyridyl)-2-propenyl]-8-(t-butyldimethylsiloxy)-octanoate → HCID 10410741, compound

HRID 465568Notes

Reaction equation

HRID 465568 reaction equation
[CH3:1][C:2]([CH3:30])([CH2:7][CH:8]([CH2:21][CH:22]=[CH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH2:9][CH2:10][CH2:11][CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C:3]([O:5][CH3:6])=[O:4]>C(O)C.[Pd]>[CH3:1][C:2]([CH3:30])([CH2:7][CH:8]([CH2:21][CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH2:9][CH2:10][CH2:11][CH2:12][O:13][Si:14]([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:15])[CH3:16])[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 1

HCID 67916587Methyl 2,2-dimethyl-4-[3-(3-pyridyl)-2-propenyl]-8-(t-butyldimethylsiloxy)-octanoate

Product 1

HCID 10410741HCID 10410741, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1.83 g of methyl 2,2-dimethyl-4-[3-(3-pyridyl)-2-propenyl]-8-(t-butyldimethylsilyloxy)-octanoate in 50 ml ethanol is added 0.18 g of 10% palladium on carbon. The mixture is hydrogenated at 3 atmospheres (=3.04 bar) pressure in a Parr apparatus for 7.5 h. The catalyst is filtered off and washed with ethanol. The solvent is evaporated to give methyl 2,2-dimethyl-4-[3-(3-pyridyl)propyl]-8-(t-butyldimethylsilyloxy)-octanoate as an oil, NMR (CDCl3): delta 3.58 (s,3H), 3.55 (t,2H), 2.57 (t,2H), 1.13 (s,6H).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with ethanol
  3. customThe solvent is evaporated

Sources & evidence

ORD record
ord-2f761af0e9c249a6a5000231fa40e350
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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