3-Pyridinecarboxaldehyde → N-(3-picolyl) D-leucine methyl ester

HRID 355447Notes

Reaction equation

HRID 355447 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].C([O-])(=O)C.[Na+].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1.C([BH3-])#N.[Na+]>CO>[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH:6][CH2:23][C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 11600782D-Leucine Methyl Ester Hydrochloride

Product 1

HCID 54454922N-(3-picolyl) D-leucine methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

D-Leucine methyl ester hydrochloride (20 g, 110.43 mmol) is dissolved in methanol. To this is added sodium acetate (22.64 g, 276 mmol) followed by 3-pyridine carboxaldehyde (10.9 mL, 115.5 mmol). The mixture is allowed to stir at room temperature for 15 minutes and then sodium cyanoborohydride (4.15 g, 66 mmol) is added slowly over 15 minutes. After stirring for 16 hours at room temperature methanol is evaporated under reduced pressure and the resulting oil is taken up in ethyl acetate and washed with water (2×). The organics are dried over sodium sulfate and concentrated to an oil. The product is purified by silica gel flash chromatography (100% ethyl acetate) to give N-(3-picolyl) D-leucine methyl ester as an oil.

Workup

  1. customis evaporated under reduced pressure
  2. washwashed with water (2×)
  3. dry with materialThe organics are dried over sodium sulfate
  4. concentrationconcentrated to an oil
  5. customThe product is purified by silica gel flash chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-9c4e9c517b76469c8439711d17219282
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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