Acetic Acid → HCID 49848908, compound

HRID 1404435Notes

Reaction equation

HRID 1404435 reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].[Li].[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][C:18]1=[O:22].C(Br)CC.C(O)(=O)C>C1COCC1>[CH2:2]([CH:19]1[CH2:20][CH2:21][N:17]([CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=2)[C:18]1=[O:22])[CH2:1][CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78401-BromopropaneHCID 1266787HCID 1266787, compoundHCID 45051747Lithium diisopropylamine

Product 1

HCID 49848908HCID 49848908, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a 2 M lithium diisopropylamine solution in THF of −78° C. is added 1-(2-(pyridin-2-yl)-ethyl)pyrrolidin-2-one 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 3-propyl-1-(2-(pyridin-2-yl)ethyl)pyrrolidin-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-254e455f6cf44ef194a54eee09af7e3a
Source dataset
uspto-grants-2014_12
Patent number
US08912329B2

Reaction notes

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