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

HRID 428587

Reaction equation

HRID 428587 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10](O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[F-:25].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([F:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86583595(R)-1-Benzyl-3-pyrrolidinol tosylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-1-benzyl-3-pyrrolidinol-tosylate (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 (100mix2). 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 (100mix2)
  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-ea4de7219b4046fd92e2d8cd81bd5517
Source dataset
uspto-grants-2001_11
Patent number
US06313302B2

Linked notes

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