p-Toluenesulfonic acid monohydrate → Pyrrolidine, 1-[2-(5-fluoro-3,4-dihydro-2-naphthalenyl)ethyl]-

HRID 1457312Notes

Reaction equation

HRID 1457312 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH:7]2O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6]([CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1)=[CH:7]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22104516HCID 22104516, compound

Product 1

HCID 9816302Pyrrolidine, 1-[2-(5-fluoro-3,4-dihydro-2-naphthalenyl)ethyl]-Yield 67.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-fluoro-1,2,3,4-tetrahydro-2-[2-(1-pyrrolidinyl)ethyl]-1-naphthalenol (20.0 g) in toluene (250 ml) was added p-toluenesulfonic acid. monohydrate (16.2 g), and the mixture was refluxed overnight. After cooling, the reaction solution was washed successively with 1N aqueous sodium hydroxide solution, water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate=5:1), and the fractions containing the desired compound were combined, concentrated under reduced pressure to give the desired compound (12.6 g), as an oily product.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperatureAfter cooling
  3. washthe reaction solution was washed successively with 1N aqueous sodium hydroxide solution, water
  4. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate=5:1)
  7. additionthe fractions containing the desired compound
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e0df561e7f64475591a2fdb52c7d81f3
Source dataset
uspto-grants-1998_12
Patent number
US05847159

Reaction notes

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