Benzenepropanal → Ethyl 2-butyl-3-[4-[2-(3-phenylpropylamino)ethoxy]phenyl]propionate

HRID 1860025Notes

Reaction equation

HRID 1860025 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].[NH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([CH2:32][CH2:33][CH2:34][CH3:35])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][CH:20]=1>C(O)(=O)C.C(O)C>[CH2:32]([CH:26]([CH2:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH2:16][NH:15][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:20][CH:21]=1)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 3

HCID 7707BenzenepropanalHCID 5003444Sodium cyanoborohydrideHCID 18625891Ethyl 3-[4-(2-aminoethoxy)phenyl]-2-butylpropionate

Product 1

HCID 18625950Ethyl 2-butyl-3-[4-[2-(3-phenylpropylamino)ethoxy]phenyl]propionate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

3-phenylpropionaldehyde (0.23 ml), sodium cyanoborohydride (117 mg) and acetic acid (one drop) were added to a solution of ethyl 3-[4-(2-aminoethoxy)phenyl]-2-butylpropionate (500 mg), which is the product of Reference example 6, in ethanol (10 ml). The mixture was stirred at ambient temperature for 18 hours. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on silica gel column using dichloromethane/methanol=19/1 as the eluant to afford the desired compound (460 mg) as a pale yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe layers were separated
  4. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via chromatography on silica gel column

Sources & evidence

ORD record
ord-0e8cc97ea7634436a2fba62877edd338
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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