Acetic Acid → N-benzyl-3-pyrrolidinol

HRID 1662086Notes

Reaction equation

HRID 1662086 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[CH2:5]([N:12]1[CH2:16][CH2:15][C@@H:14](N)[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(OCC)(=O)C>[CH2:5]([N:12]1[CH2:16][CH2:2][CH:1]([OH:4])[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:5]([N:12]1[CH2:16][CH:15]=[CH:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 1519354(3R)-1-benzylpyrrolidin-3-amine

Product 2

HCID 69889N-benzyl-3-pyrrolidinolHCID 5615061-Benzyl-2,5-dihydropyrrole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

When 960 mg of acetic acid (16 mmol) was added to a solution in ethyl acetate (30 mL) of 3.6146 g of crude (R)-1-benzyl-3-aminopyrrolidine produced in the step 1-1 (14.6 mmol, optical purity: 92.4% e.e., including 29.5% by weight 1-benzyl-3-pyrrolidinol, and 0.8% by weight 1-benzyl-2,5-dihydro-1H-pyrrole as impurities), a crystal was precipitated. After stirring at 5° C. for 30 min, the crystal was filtrated under reduced pressure, which was washed with 20 mL of ethyl acetate, and thereafter vacuum drying was carried out to give a white crystal of 2.5804 g (yield: 75%, optical purity: 94.3% e.e., with no 1-benzyl-3-pyrrolidinol and 1-benzyl-2,5-dihydro-1H-pyrrole detected).

Sources & evidence

ORD record
ord-26115ace62d0463aa40e744cd9619b5e
Source dataset
uspto-grants-2011_10
Patent number
US08030501B2

Reaction notes

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