Pyrrolidine → HCID 59333039, compound

HRID 1695197Notes

Reaction equation

HRID 1695197 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][O:7][C:8](=[O:14])[CH:9]([CH3:13])[CH2:10][CH2:11]Br>C1(C)C=CC=CC=1>[CH3:6][O:7][C:8](=[O:14])[CH:9]([CH3:13])[CH2:10][CH2:11][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 11745547methyl 4-bromo-2-methylbutanoate

Product 1

HCID 59333039HCID 59333039, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Pyrrolidine (5.4 mL, 66 mmol) was dissolved in toluene (40 mL). 4-Bromo-2-methyl-butyric acid methyl ester (4.3 g, 22.0 mmol) was added and the reaction stirred at reflux for 2.5 hours. Removal of the solvent and of the excess amine at reduced pressure gave 2-methyl-4-(pyrrolidin-1-yl)-butyric acid methyl ester as a thick oil. The crude product was diluted with MeOH (3 mL) and 1.0M NaOH aq solution (22 mL) was added and the reaction stirred at reflux for 18 hours.

Workup

  1. temperatureat reflux for 2.5 hours
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-666fc3914ece4f5a9975decf5ce8e5ca
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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