Water → rac-(3R,4S)-1-benzylpyrrolidine-3,4-diol

HRID 366882

Reaction equation

HRID 366882 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:14].[OH2:18].C1C=C(Cl)C=C(C(OO)=O)C=1>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([OH:18])[CH:10]([OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 70297m-Chloroperbenzoic acidHCID 5615061-Benzyl-2,5-dihydropyrrole

Product 1

HCID 536645rac-(3R,4S)-1-benzylpyrrolidine-3,4-diolYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 12.0 g (0.12 mol) of 98% sulfuric acid, 15.0 g of water, and 60.0 g of acetone in a round flask reactor, 31.1 g (0. 13 mol) of 70% m-CPBA (m-chloroperbenzoic acid produced by Tokyo Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 10 hours at 40° C. without irradiation by lamps. After completion, acetone was evaporated under reduced pressure, neutralized by NaOH (aq), and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 17.4 g of 1-benzyl-3,4-dihydroxypyrrolidine (yield 90.0%) was obtained.

Workup

  1. customto react for 10 hours at 40° C. without irradiation by lamps
  2. customAfter completion, acetone was evaporated under reduced pressure
  3. extractionextracted with toluene and water
  4. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-df62f8cc96aa4995bda024e459f79a66
Source dataset
uspto-grants-2000_10
Patent number
US06130338

Linked notes

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