Acetic Acid → HCID 49848907, compound

HRID 1404433Notes

Reaction equation

HRID 1404433 reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].[Li].[C:9]1([CH:15]([N:17]2[CH2:21][CH2:20][CH2:19][C:18]2=[O:22])C)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:23](Br)CC.C(O)(=O)C>O1CCCC1>[CH2:15]([N:17]1[CH2:21][CH2:20][CH:19]([CH2:2][CH2:1][CH3:3])[C:18]1=[O:22])[CH2:9][C:14]1[CH:23]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78401-BromopropaneHCID 38151651-(1-phenylethyl)pyrrolidin-2-oneHCID 45051747Lithium diisopropylamine

Product 1

HCID 49848907HCID 49848907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a 2 M lithium diisopropylamine solution in tetrahydrofuran of −78° C. is added 1-phenylethyl-2-pyrrolidone and the mixture is stirred for 1.5 h at −78° C. Then 1-propyl bromide is added and the reaction is stirred for another 1.5 h at −78° C. The reaction mixture is allowed to warm up to 0° C. before ice-cold water with acetic acid is added and subsequently extracted 3 times with dichloromethane. The dichloromethane is concentrated in vacuo and the residue is dissolved in dichloromethane, washed with saturated NaHCO3 and brine. Crude 1-phenethyl-3-propylpyrrolidin-2-one is obtained after removal of the solvents in vacuo. The product is purified by column chromatography.

Workup

  1. stirringthe reaction is stirred for another 1.5 h at −78° C
  2. additionis added
  3. extractionsubsequently extracted 3 times with dichloromethane
  4. concentrationThe dichloromethane is concentrated in vacuo
  5. dissolutionthe residue is dissolved in dichloromethane
  6. washwashed with saturated NaHCO3 and brine

Sources & evidence

ORD record
ord-8f3292de930d458f924ad4e279e7205b
Source dataset
uspto-grants-2014_12
Patent number
US08912329B2

Reaction notes

Loading…