Triethylamine → HCID 43725938, compound

HRID 899955Notes

Reaction equation

HRID 899955 reaction equation
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1.Cl.[NH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20].[BH4-].[Na+]>ClC(Cl)C.CO>[CH3:23][C:18]([NH:17][CH2:14][C:11]1[CH:10]=[CH:9][N:8]=[CH:13][CH:12]=1)([CH3:24])[C:19]([O:21][CH3:22])=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 43725938HCID 43725938, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

1.04 ml of triethylamine and then 0.659 g of pyridine-4-carbaldehyde are successively added to a solution of 0.945 g of methyl α-aminoisobutyrate hydrochloride in 28 ml of dichloroethane. The reaction mixture is stirred overnight at a temperature in the region of 20° C. The mixture is purified by filtration on Merck Lichroprep aminopropyl-grafted silica. The filtrate is concentrated under reduced pressure and the residue thus obtained is taken up in 25 ml of methanol, 0.372 g of sodium borohydride is added. The reaction mixture is stirred for 48 hours at a temperature in the region of 20° C. and then poured into a mixture of a normal solution of sodium hydroxide/ice. The mixture obtained is extracted three times with ethyl acetate. The organic phase is dried over magnesium sulfate and then concentrated under reduced pressure. 0.726 g of methyl 2-methyl-2-[(pyrid-4-ylmethyl)amino]propanoate is thus obtained in the form of an oil, the characteristics of which are as follows:

Workup

  1. filtrationThe mixture is purified by filtration on Merck Lichroprep aminopropyl-grafted silica
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue thus obtained
  4. stirringThe reaction mixture is stirred for 48 hours at a temperature in the region of 20° C.
  5. customThe mixture obtained
  6. extractionis extracted three times with ethyl acetate
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4643047916cb4db197e6bf2ccbd7a8cc
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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