1-Methyl-1,4-cyclohexadiene → HCID 86722311, compound

HRID 874820Notes

Reaction equation

HRID 874820 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][N:8](CC1C=CC=CC=1)[CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].CC1CC=CCC=1>C(O)C.[Pd]>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 780061-Methyl-1,4-cyclohexadieneHCID 86722309HCID 86722309, compound

Product 1

HCID 86722311HCID 86722311, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of N-(2-(1,3-dioxolan-2-yl)ethyl)-N-benzyl-2-((tert-butyldimethylsilyl)oxy)ethanamine (3.87 g, 10.6 mmol) in ethanol (100 mL) was added 10% palladium on carbon (1.93 g) and 1-methyl-1,4-cyclohexadiene (5.93 mL, 53.0 mmol). The suspension was heated at reflux for 30 minutes and allowed to cool. The suspension was filtered through celite and the filter cake washed with further ethanol. The solvent was evaporated at reduced pressure to afford the title compound (2.64 g, 91%).

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 30 minutes
  3. temperatureto cool
  4. filtrationThe suspension was filtered through celite
  5. washthe filter cake washed with further ethanol
  6. customThe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-c411ac4acbf94616b507fb77c7f65ae3
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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