Carbon Dioxide → HCID 15079752, compound

HRID 928351Notes

Reaction equation

HRID 928351 reaction equation
[Li]CCCC.CCCCCC.[CH3:12][N:13]([CH3:17])[CH2:14][C:15]#[CH:16].[C:18](=[O:20])=[O:19]>C1COCC1.CO.O>[CH3:12][N:13]([CH3:17])[CH2:14][C:15]#[C:16][C:18]([OH:20])=[O:19]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 8058HexaneHCID 81643N,N-DimethylpropargylamineHCID 178418339Butyllithium

Product 1

HCID 15079752HCID 15079752, compoundYield 106.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-BuLi in hexane (2.5M, 24.06 mmol, 9.62 mL) was slowly added to a solution of N,N-dimethylprop-2-yn-1-amine (24.06 mmol, 2.59 mL, 2 g) in dry THF (10 mL) at −78° C. The mixture was stirred for 1 h at −78° C., then crushed CO2 (241 mmol, 10.59 g) was added in one portion and the reaction mixture was stirred for an additional 10 min. The resulting solution was poured into water and washed with ethyl acetate. The aqueous layer was evaporated in vacuo to give the crude amino acid. This was dissolved in methanol, and the insoluble salts were removed via filtration. The filtrate was evaporated to give 3.25 g of 4-(dimethylamino)but-2-ynoic acid (106%).

Workup

  1. stirringthe reaction mixture was stirred for an additional 10 min
  2. washwashed with ethyl acetate
  3. customThe aqueous layer was evaporated in vacuo
  4. customto give the crude amino acid
  5. customthe insoluble salts were removed via filtration
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b877b0637c044dd386a24c68ea021e11
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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