2-Bromonaphthalene → HCID 18689909, compound

HRID 1871909Notes

Reaction equation

HRID 1871909 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C([Li])CCC.[CH3:17][N:18]1[CH:22]2[CH2:23][C:24]([CH2:26][CH:19]1[CH2:20][CH2:21]2)=[O:25]>O1CCCC1>[OH:25][C:24]1([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=2)[CH2:23][CH:22]2[N:18]([CH3:17])[CH:19]([CH2:20][CH2:21]2)[CH2:26]1

Participants

5

Reactant 3

HCID 113722-BromonaphthaleneHCID 79038Npc164516HCID 178418339Butyllithium

Product 1

HCID 18689909HCID 18689909, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 5.0 gm (24.1 mMol) 2-bromonaphthalene in 80 mL tetrahydrofuran was cooled to -78° C. To this solution was then added 15.8 mL (25.3 mMol) n-butyllithium (1.6M in tetrahydrofuran) followed by a solution of 4.03 gm (29 mMol) 3-tropinone in 35 mL tetrahydrofuran. The reaction mixture was stirred at -78° C. for 2 hours and was then allowed to warm gradually to room temperature. The reaction mixture quenched by the addition of saturated aqueous ammonium chloride. The resulting mixture was extracted well with ethyl acetate. The organic phases were combined, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing from 2-10% methanol and 30% dichloromethane saturated with ammonia. Fractions containing product were combined and concentrated under reduced pressure to provide 3.2 gm (50%) of 3-hydroxy-3-(naphth-2-yl)-8-methyl-8-azabicyclo[3.2.1]octane.

Workup

  1. temperatureto warm gradually to room temperature
  2. customThe reaction mixture quenched by the addition of saturated aqueous ammonium chloride
  3. extractionThe resulting mixture was extracted well with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with dichloromethane containing from 2-10% methanol and 30% dichloromethane saturated with ammonia
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e99ad5ad21f4877810dc101eebe6d65
Source dataset
uspto-grants-2000_08
Patent number
US06107307

Reaction notes

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