Carbon Dioxide → (4-pyrrolidin-1-ylmethylphenyl)propynoic Acid

HRID 735006Notes

Reaction equation

HRID 735006 reaction equation
C([Li])CCC.[C:6]([C:8]1[CH:19]=[CH:18][C:11]([CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:10][CH:9]=1)#[CH:7].[C:20](=[O:22])=[O:21].Cl>CCCCCC.C1COCC1>[N:13]1([CH2:12][C:11]2[CH:18]=[CH:19][C:8]([C:6]#[C:7][C:20]([OH:22])=[O:21])=[CH:9][CH:10]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 860607941-(4-Ethynylbenzyl)pyrrolidineHCID 178418339Butyllithium

Product 1

HCID 68819317(4-pyrrolidin-1-ylmethylphenyl)propynoic Acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

5.98 mL (14.85 mmol) of a 1.6M butyllithium solution in n-hexane is added dropwise to a solution of 2.3 g (12.41 mmol) of 1-(4-ethynylbenzyl)pyrrolidine in 50 mL of THF at −78° C. and stirred for 1 hour at this temperature. Then dry ice is added to the reaction mixture. Then the reaction mixture is allowed to come up to ambient temperature and stirred for 14 hours. The reaction mixture is combined with dilute hydrochloric acid and extracted with dichloromethane. The organic phase is separated off and dried over sodium sulfate. The sodium sulfate is separated off and the solvent is removed. Yield: 0.3 g (10.5% of theory); C14H15NO2 (M=229.28); calc.: molecular ion peak (M+H)+: 230; found: molecular ion peak (M+H)+: 230; Rf value: 0.15 (silica gel, dichloromethane/methanol/ammonia (9:1:0.1)).

Workup

  1. customto come up to ambient temperature
  2. stirringstirred for 14 hours
  3. extractionextracted with dichloromethane
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulfate
  6. customThe sodium sulfate is separated off
  7. customthe solvent is removed

Sources & evidence

ORD record
ord-a364a150ddeb475594ab3264fb33fcd9
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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