Hexanal → N-hexyl-D-alanine methyl ester

HRID 355455Notes

Reaction equation

HRID 355455 reaction equation
[CH3:1][O:2][C:3](=[O:7])[C@@H:4]([CH3:6])[NH2:5].[CH:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3](=[O:7])[C@@H:4]([CH3:6])[NH:5][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 6184HexanalHCID 89020methyl D-alaninateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 53973081N-hexyl-D-alanine methyl esterYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

D-alanine methyl ester (1.5 g, 10.75 mmol) is taken up in 50 mL methanol and is cooled to 0° C. To this is added hexanal (1.3 mL, 10.75 mmol) followed by sodium acetate (2.62 g, 32 mmol). After stirring for 15 minutes at 0° C. sodium cyanoborohydride (440 mg, 7 mmol) is added and the mixture is stirred for further 16 hours at room temperature. The methanol is evaporated and the resulting residue is taken up in ether and is transferred to a separatory funnel, washed with water (2×), dried over sodium sulfate, and is evaporated to give 1.81 g of N-hexyl-D-alanine methyl ester as a colorless oil.

Workup

  1. additionis added
  2. customThe methanol is evaporated
  3. customis transferred to a separatory funnel
  4. washwashed with water (2×)
  5. dry with materialdried over sodium sulfate
  6. customis evaporated

Sources & evidence

ORD record
ord-53fd62c5d8fe4f6c87d15f21d9d40eeb
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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