Carbon Tetrachloride → (S)-1-Benzyl-3-chloropyrrolidine

HRID 1597394Notes

Reaction equation

HRID 1597394 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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:34]>>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([Cl:34])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 53640613(S)-1-Benzyl-3-chloropyrrolidineYield 72%

Procedure

To a stirred solution of (R)-1-benzyl-3-pyrrolidinol (886 mg, 5.0 mmol) in CCl4(20 ml) was added triphenylphosphine(1.574 g, 6.0 mmol) at rt. After 20 h stirring at reflux temperature, the solvent was evaporated. Saturated NaHCO3 aqueous solution and water was added to the residue, and the mixture was extracted with AcOEt. The extract was brine, dried(Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel; 100 g, CH2Cl2/MeOH: 50/1-45/1) to give 706 mg(72%) of pale yellow oil.

Workup

  1. temperatureat reflux temperature
  2. customthe solvent was evaporated
  3. additionSaturated NaHCO3 aqueous solution and water was added to the residue
  4. extractionthe mixture was extracted with AcOEt
  5. concentrationconcentrated
  6. customto give brown oil, which
  7. customwas purified by column chromatography (silica gel; 100 g, CH2Cl2/MeOH: 50/1-45/1)

Sources & evidence

ORD record
ord-9303aa1f90ca4bb59edcf6b536c0f39f
Source dataset
uspto-grants-2001_09
Patent number
US06294569B2

Reaction notes

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