Triethylamine → (1R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]oct-3-en-2-one

HRID 1017260Notes

Reaction equation

HRID 1017260 reaction equation
[Br-].[CH2:2]([N+:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[C:10]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:22]([S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25])=[CH2:23].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH2:2]([N:9]1[C@@H:14]2[C@H:22]([S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:25])=[O:26])[CH2:23][C@@:10]1([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11](=[O:15])[CH:12]=[CH:13]2)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 79664Phenyl vinyl sulfoneHCID 516892Sodium BicarbonateHCID 21931695N-benzyl-3-hydroxy-2-phenylpyridinium bromide

Product 1

HCID 69686040(1R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]oct-3-en-2-oneYield 78.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-benzyl-3-hydroxy-2-phenylpyridinium bromide (Description 5; 4.91 g, 14.3 mmol), phenyl vinyl sulphone (4.2 g, 25 mmol), triethylamine (2.8 ml, 20 mmol) and 1,4-dioxane (50 ml) was heated at reflux overnight. After cooling to room temperature, the reaction mixture was poured onto saturated aqueous NaHCO3 and extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 10-70%) to give the title compound (4.84 g, 78%) as a yellow-orange foam. Crystallisation from iso-hexane:diethyl ether gave the product as yellow rhombs.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 10-70%)

Sources & evidence

ORD record
ord-8845ab01da8e4bfc9ee0a22c1cca99d6
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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