Acetic Acid → HCID 49849018, compound

HRID 1404439Notes

Reaction equation

HRID 1404439 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][CH:16]1[NH:20][C:19](=[O:21])[CH2:18][CH2:17]1.C(Br)CC.C(O)(=O)C>C1COCC1>[CH2:2]([CH:18]1[CH2:17][CH:16]([CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=2)[NH:20][C:19]1=[O:21])[CH2:1][CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78401-BromopropaneHCID 45051747Lithium diisopropylamineHCID 67290424HCID 67290424, compound

Product 1

HCID 49849018HCID 49849018, 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 5-(pyridin-2-ylmethyl)pyrrolidin-2-one, and the mixture is stirred for 1.5 hours at −78° C. Then 1-propyl bromide is added and the reaction is stirred for another 1.5 hours 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-5-(pyridin-2-ylmethyl)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 hours 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-31f8ad3493864a1995d6bed92bf36e7a
Source dataset
uspto-grants-2014_12
Patent number
US08912329B2

Reaction notes

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