Benzenepropanal → HCID 54316277, compound

HRID 847622Notes

Reaction equation

HRID 847622 reaction equation
[CH:1](=O)[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.Cl.[CH2:13]([O:20][C:21](=[O:27])[C@H:22]([CH:24]([CH3:26])[CH3:25])[NH2:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>C(O)(C)C>[CH2:13]([O:20][C:21](=[O:27])[C@H:22]([CH:24]([CH3:25])[CH3:26])[NH:23][CH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7707BenzenepropanalHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydride2×HCID 70043269HCID 70043269, compound

Product 1

HCID 54316277HCID 54316277, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of dihydrocinnamaldehyde (7 mmol), valine benzyl ester dihydrochloride (7 mmol), anhydrous sodium acetate (0.7 g, 21 mmol), and sodium cyanoborohydride (11 mmol) in 200 mL of isopropyl alcohol was stirred at ambient temperature. After 16 h, an additional 0.2 g portion of sodium cyanoborohydride was added and stirring was continued for 4.5 h. After removal of the solvent in vacuo, the residue was taken up in ethyl acetate, washed sequentially with saturated aqueous NaHCO3 and saturated brine, dried over MgSO4, and concentrated. Silica gel chromatography gave the desired compound.

Workup

  1. stirringstirring
  2. waitwas continued for 4.5 h
  3. customAfter removal of the solvent in vacuo
  4. washwashed sequentially with saturated aqueous NaHCO3 and saturated brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cde7ffeac45e438ba8559de94d0d3a1b
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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