Tridecanal → Methyl 3-tridecylaminopropionate

HRID 1872802Notes

Reaction equation

HRID 1872802 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].Cl.[NH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>CO>[CH2:1]([NH:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 25311TridecanalHCID 517045Sodium AcetateHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18687169Methyl 3-tridecylaminopropionateYield 54.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cooled solution of tridecanal (1.0 g), methyl 3-aminopropionate hydrochloride (704 mg), and sodium acetate (414 mg) in methanol (20 ml) was added sodium cyanoborohydride (317 mg). After stirring for 45 minutes, the mixture was quenched with water (20 ml), concentrated, and extracted with ethyl acetate (40 ml). The organic phase was washed with brine, dried, and concentrated under reduced pressure. The residue was purified on silica gel, eluting with 5% methanol in chloroform to give methyl 3-tridecylaminopropionate (0.78 g).

Workup

  1. customthe mixture was quenched with water (20 ml)
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate (40 ml)
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified on silica gel
  8. washeluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-e5abfdbc0abf41a093719ba20cb5e680
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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