Sulfuric Acid → 1-Benzyl-4-methylpyrrolidin-3-ol

HRID 366891Notes

Reaction equation

HRID 366891 reaction equation
[CH2:1]([N:8]1[CH2:12]C=C[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:18]1[CH2:22][O:21]C[CH2:19]1.C[Li]>C(OCC)C.O>[CH2:1]([N:8]1[CH2:12][CH:18]([CH3:19])[CH:22]([OH:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 5615061-Benzyl-2,5-dihydropyrroleHCID 178418348HCID 178418348, compound

Product 1

HCID 159347591-Benzyl-4-methylpyrrolidin-3-olYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

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, and 60.0 g of THF in a quartz round flask reactor, 45.6 g (0.20 mol) of (NH4)2S2O8 (ammonium peroxydisulfate produced by Mitsubishi Gas Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 5 days at room temperature with irradiation by 500 W Xe lamps (UXL-500D xenon lamp produced by Ushio). 300 mL (0.30 mol) of 1 mol/L methyllithium (MeLi) in diethyl ether solution (produced by Kanto Chemical Co., Inc.) was continuously added to the reaction mixture and stirred for 5 hours at about 5° C. using an ice-bath. After completion, water was added to destroy excess MeLi at about 5° C. using an ice-bath. Acetone and diethyl ether were evaporated under reduced pressure, and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 14.5 g of 1-benzyl-4-methyl-3-pyrrolidinol (yield 76.0%) was obtained.

Workup

  1. customto react for 5 days at room temperature with irradiation by 500 W Xe lamps (UXL-500D xenon lamp produced by Ushio)
  2. stirringstirred for 5 hours at about 5° C.
  3. customto destroy excess MeLi at about 5° C.
  4. customAcetone and diethyl ether were evaporated under reduced pressure
  5. extractionextracted with toluene and water
  6. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-db5c6dc50ac6458daaa08209ed490f3b
Source dataset
uspto-grants-2000_10
Patent number
US06130338

Reaction notes

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