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

HRID 1018062Notes

Reaction equation

HRID 1018062 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.[OH2:13].[OH2:14].C1(C)C=C(C)C=C(C)C=1S(O)(=O)=O.O.C1C=C(Cl)C=C(C(OO)=O)C=1>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([OH:13])[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 70297m-Chloroperbenzoic acidHCID 5615061-Benzyl-2,5-dihydropyrroleHCID 156203442-Mesitylenesulfonic acid dihydrate

Product 1

HCID 536645rac-(3R,4S)-1-benzylpyrrolidine-3,4-diolYield 85.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 15.9 g (0.1 mol) of l-benzyl-3-pyrroline, 56.7 g (0.24 mol) of 2-mesitylenesulfonic acid dihydrate (produced by Aldrich Chemical Co., Inc.), 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, 16.6 g of 1-benzyl-3,4-dihydroxypyrrolidine (yield 85.9%) 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-de28a545e0ee40f398dc5b5df75a8c2a
Source dataset
uspto-grants-2002_11
Patent number
US06479668B1

Reaction notes

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