Water → (S)-1-Benzyl-3-chloropyrrolidine

HRID 1532258Notes

Reaction equation

HRID 1532258 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([O-])(O)=O.[Na+].O.C(Cl)(Cl)(Cl)[Cl:40]>>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([Cl:40])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 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 evapolated. 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. extractionthe mixture was extracted with AcOEt
  3. concentrationconcentrated
  4. customto give brown oil, which
  5. customwas purified by column chromatography (silica gel; 100 g, CH2Cl2/MeOH: 50/1-45/1)

Sources & evidence

ORD record
ord-4549116e471840b7b870aa771a643d17
Source dataset
uspto-grants-2001_03
Patent number
US06201007B1

Reaction notes

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