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

HRID 428590

Reaction equation

HRID 428590 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-6f249b707abc470fa69a44fb6b709c7c
Source dataset
uspto-grants-2001_11
Patent number
US06313302B2

Linked notes

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