Toluene → 8-Phenyl-1,4-dioxa-8-azaspiro[4.5]decane

HRID 2364100Notes

Reaction equation

HRID 2364100 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CC([O-])(C)C.[Na+].Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(C)C=CC=CC=1>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C(=CC=CC=2)C=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:18]1([N:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 7961BromobenzeneHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 23676156Sodium t-butoxide

Product 1

HCID 114700398-Phenyl-1,4-dioxa-8-azaspiro[4.5]decaneYield 99.4%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1,4-dioxa-8-azaspiro[4.5]decane (0.65 mL, 5.0 mmol), 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphane) (255 mg, 0.375 mmol), sodium 2-methylpropan-2-olate (1.44 g, 15 mmol), bromobenzene (0.684 mL, 6.5 mmol), tris(dibenzylideneacetone) dipalladium(0) (114 mg, 0.125 mmol) and toluene (15 mL) was stirred at 110° C. for 5 h under Ar atmosphere. Water was added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, 90:10 hexane/EtOAc to 50:50 hexane/EtOAc) to give the title compound (1.09 g, 99%) as an orange oil:

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe organic materials were extracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customAfter removal of the solvent at reduced pressure
  8. customthe residue was purified by column chromatography (Purif, silica gel, 90:10 hexane/EtOAc to 50:50 hexane/EtOAc)

Sources & evidence

ORD record
ord-cb31e9025ae5438b832e418a943d5c7e
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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