Selectfluor → HCID 23234366, compound

HRID 1912525Notes

Reaction equation

HRID 1912525 reaction equation
[CH3:1][C:2]1([CH3:10])[C@H:8]2[CH2:9][C@@H:3]1[CH2:4][CH2:5][C:6]2=[O:7].S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+].[F:29][B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2.F[B-](F)(F)F>O>[F:29][C@@H:5]1[CH2:4][C@H:3]2[CH2:9][C@H:8]([C:2]2([CH3:10])[CH3:1])[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 2724933SelectfluorHCID 3423265Sodium Lauryl SulfateHCID 10313167(1R,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-one

Product 1

HCID 23234366HCID 23234366, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (+)-nopinone (Aldrich, 1.0 g, 7.2 mmol) in water (35 mL), was added sodium dodecyl sulfate (Aldrich, 2.1 g, 7.2 mmol). The mixture was heated to 80° C. and then 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane tetrafluoroborate (Alfa-aesar, 2.8 g, 8.0 mmol) was added in two portions with one hour interval and stirred at 80° C. overnight. The reaction mixture was cooled and extracted with diethyl ether (3×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 0-20% of ethyl acetate in hexanes) to obtain 0.4 g of the title compound. MS (DCI/NH3) m/z 174 (M+NH4)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with diethyl ether (3×30 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (SiO2, 0-20% of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b8518192650f482ba449e0b6fc425806
Source dataset
uspto-grants-2013_12
Patent number
US08609674B2

Reaction notes

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