Propanal → Diethyl 2-(propylamino)malonate

HRID 327434

Reaction equation

HRID 327434 reaction equation
[NH2:1][CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].[CH:17](=O)[CH2:18][CH3:19].C([BH3-])#N.[Na+]>C(O)C>[CH2:17]([NH:1][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 527Propanal2×HCID 81272Propanedioic acid, 2-amino-, 1,3-diethyl esterHCID 2723922Sodium ethoxideHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 15122388Diethyl 2-(propylamino)malonateYield 115.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl aminomalonate (21.1 g, 0.1 mol) was dissolved in ethanol and sodium ethoxide in ethanol (50 mL of 1 M) was added. Propionaldehyde (6.6 g, 0.11 mol) and sodium cyanoborohydride (3.6 g, 0.058 mol) were added to the stirred solution. After 30 minutes additional propionaldehyde (6.0 g) and sodium cyanoborohydride (2.6 g) were added to complete the reaction. The solution was evaporated, and the residue was partitioned between ethyl acetate and water. Evaporation of the ethyl acetate gave 25.1 g of diethyl (propylamino)malonate. This was mixed with di t-butyl dicarbonate (34 g, 0.156 mol) and the mixture was heated at 100° C. for 1 hour. The crude product was chromatographed on silica gel using ethyl acetate:hexane as the eluant to give 21.2 g of diethyl (N-(1,1-dimethylethoxycarbonyl)propylamino)malonate as an oil.

Workup

  1. customthe reaction
  2. customThe solution was evaporated
  3. customthe residue was partitioned between ethyl acetate and water
  4. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-35f630e260f24b428d85bf7fb1e5a8d5
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Linked notes

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