3-Pyridinecarboxaldehyde → HCID 53885487, compound

HRID 1280391Notes

Reaction equation

HRID 1280391 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[C@@H:5]([CH3:7])[NH2:6].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=O)[CH:10]=1.C([BH3-])#N.[Na+]>CO>[CH3:2][O:3][C:4](=[O:8])[C@@H:5]([CH3:7])[NH:6][CH2:15][C:11]1[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11182647Methyl D-alaninate hydrochloride

Product 1

HCID 53885487HCID 53885487, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Part A: To a solution of D-alanine methyl ester hydrochloride (6.0 grams) in methanol (25 mL) is added 1.1 equivalents of 3-Pyridinecarboxaldehyde. The solution is stirred at room temperature for several hours and then the solvent removed by rotary evaporation. The resulting imine is redissolved in acetic acid (10 mL) and methanol (2 mL), and sodium cyanoborohydride (1.5 equivalents) is added in several portions over 10 minutes. The mixture is then stirred for 16 hours and then concentrated by rotary evaporation. The resulting residue is partitioned between ethyl acetate and aqueous sodium carbonate (10%). The organic layer is dried over magnesium sulfate, filtered and concentrated to yield the desired N-3-picolyl-D-alanine methyl ester.

Workup

  1. customthe solvent removed by rotary evaporation
  2. dissolutionThe resulting imine is redissolved in acetic acid (10 mL)
  3. stirringThe mixture is then stirred for 16 hours
  4. concentrationconcentrated by rotary evaporation
  5. customThe resulting residue is partitioned between ethyl acetate and aqueous sodium carbonate (10%)
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d47b28283cf84a518f5a7d5ac165bf12
Source dataset
uspto-grants-2002_09
Patent number
US06451791B1

Reaction notes

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