3-Nitrophenylboronic Acid → HCID 57054725, compound

HRID 581221Notes

Reaction equation

HRID 581221 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH:4]=[C:5](OS(C(F)(F)F)(=O)=O)[CH2:6]2.[Cl-].[Li+].[N+:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH:4]=[C:5]([C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:20]([O-:22])=[O:21])[CH:28]=1)[CH2:6]2

Participants

7

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 11993054(-)-8-methyl-3-(trifluoromethylsulfonyloxy)-8-aza-bicyclo[3.2.1]oct-2-ene

Product 1

HCID 57054725HCID 57054725, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

8-Methyl-3-trifluoromethylsulphonyloxy-8-azabicyclo[3.2.1]oct-2-ene (D9) (0.400 g, 1.48 mmol) was dissolved in DME (10 ml) and lithium chloride (0.188 g, 4.44 mmol) was added followed by 3-nitrobenzeneboronic acid (0.284 g, 1.70 mmol), and 2M sodium carbonate solution (4 ml). Argon was then bubbled through the mixture and after 5 minutes Pd(PPh3)4 (0.086 g, 0.074 mmol) was added. The mixture was then heated to reflux with stirring. After 4.5 h the reaction mixture was allowed to cool and was left at room temp. for 12 h, before being partitioned between chloroform and water. The aqueous layer was then extracted with chloroform (2×) and the combined organic layers were dried (Na2SO4) and evaporated under reduced pressure to give a brown oil that was dried in vacuo. The oil was purified by silica-gel chromatography (200:10.1, CH2Cl2MeOH:NH3 as eluant) to give the title compound as a brown oil (0.147 g, 46%).

Workup

  1. additionwas added
  2. temperatureThe mixture was then heated
  3. temperatureto reflux
  4. temperatureto cool
  5. waitwas left at room temp. for 12 h
  6. custombefore being partitioned between chloroform and water
  7. extractionThe aqueous layer was then extracted with chloroform (2×)
  8. dry with materialthe combined organic layers were dried (Na2SO4)
  9. customevaporated under reduced pressure
  10. customto give a brown oil that
  11. customwas dried in vacuo
  12. customThe oil was purified by silica-gel chromatography (200:10.1, CH2Cl2MeOH:NH3 as eluant)

Sources & evidence

ORD record
ord-58d1bc06ab4c4b2eaa3c10128b4fb9e7
Source dataset
uspto-grants-1999_07
Patent number
US05919932

Reaction notes

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