1-Octene → HCID 67032429, compound

HRID 2167858Notes

Reaction equation

HRID 2167858 reaction equation
C=CCCCCCC.B1[CH:14]2[CH2:15][CH2:16][CH2:17][CH:10]1[CH2:11][CH2:12][CH2:13]2.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:26]([N:33]1[CH2:38][CH:37]([C:39]2[CH:44]=[CH:43][C:42](Br)=[CH:41][CH:40]=2)[O:36][CH2:35][CH2:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:26]([N:33]1[CH2:34][CH2:35][O:36][CH:37]([C:39]2[CH:44]=[CH:43][C:42]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:10])=[CH:41][CH:40]=2)[CH2:38]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 5

HCID 81251-OcteneHCID 62657Potassium Phosphate, TribasicHCID 789669-Borabicyclo(3.3.1)nonaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 580978794-Benzyl-2-(4-bromo-phenyl)-morpholine

Product 1

HCID 67032429HCID 67032429, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-octene (2.12 mL, 13.5 mmol) in THF (50 mL) was added 9-BBN (4.3 g, 17.6 mmol), at 0° C. The reaction mixture was allowed to warm to RT and stirred overnight. Subsequently, K3PO4 (7.6 g, 35.8 mmol) was added, followed, after 45 minutes, by 4-benzyl-6-(4-bromo-phenyl)-morpholine (3.0 g, 9 mmol), palladium(II) acetate (80 mg; 4 mol %), and dicyclohexyl-(2′,6′-dimethoxy-biphenyl-2-yl)-phosphane (296 mg; 8 mol %). The resulting mixture was heated under reflux for 2 hours. After cooling to RT the mixture was concentrated in vacuo, the residue dissolved in EtOAc, and washed with 5% aqueous NaHCO3 solution. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O: hexanes, 1:1) to afford 4-benzyl-2-(4-octyl-phenyl)-morpholine (2.58 g).

Workup

  1. customat 0° C
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperatureAfter cooling to RT the mixture
  5. concentrationwas concentrated in vacuo
  6. dissolutionthe residue dissolved in EtOAc
  7. washwashed with 5% aqueous NaHCO3 solution
  8. dry with materialThe organic layer was dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by column chromatography (SiO2, Et2O: hexanes, 1:1)

Sources & evidence

ORD record
ord-6f71ebfd30794dba92a38f923107ba08
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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