Water → (S)-1-benzyl-3-fluoropyrrolidine

HRID 1597325Notes

Reaction equation

HRID 1597325 reaction equation
[F-:1].C([N+:6]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12][CH2:13][CH3:14])CCCC)CCC.O.[CH2:20]1[CH2:24]OC[CH2:21]1>>[CH2:15]([N:6]1[CH2:11][CH2:12][C@H:13]([F:1])[CH2:14]1)[C:16]1[CH:17]=[CH:18][CH:24]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 20694590(S)-1-benzyl-3-fluoropyrrolidineYield 71%

Procedure

To a solution of (R)-1-benzyl-3-pyrrolidinoltosylate (3.06 g, 9.24 mmol) in THF (30 ml) was added 1.0M solution of tetrabutylammonium fluoride in THF (37.0 ml, 37.0 mmol) at room temperature. After 1.5 h stirring at reflux temperature, water (150 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate (100 ml×2). The combined extract was washed with water, brine, dried (Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel: 80 g, CH2Cl2/MeOH:50/1) to afford 1.18 g (71%) of brown oil.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate (100 ml×2)
  3. extractionThe combined extract
  4. washwas washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give brown oil, which
  8. customwas purified by column chromatography (silica gel: 80 g, CH2Cl2/MeOH:50/1)

Sources & evidence

ORD record
ord-473376f47f704950b485af266f850370
Source dataset
uspto-grants-2001_09
Patent number
US06294557B1

Reaction notes

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