Diethyl bromomalonate → HCID 71273066, compound

HRID 1519683Notes

Reaction equation

HRID 1519683 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.Br[CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(#N)C>[CH:1]1([NH:4][CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 69637Diethyl bromomalonateHCID 69828Cyclopropylamine

Product 1

HCID 71273066HCID 71273066, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cyclopropylamine (0.30 mL) was added to an acetonitrile (10 mL) solution of diethyl bromopropanedioate (1.0 g), and the mixture was stirred for 16 hours at room temperature. The precipitated solid was filtered out, and the filtrate was concentrated under reduced pressure. Then, the resulting residue was purified by OH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=90/10→70/30) to obtain diethyl (cyclopropylamino)propanedioate (colorless oil) (0.57 g, 63%).

Workup

  1. filtrationThe precipitated solid was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThen, the resulting residue was purified by OH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=90/10→70/30)

Sources & evidence

ORD record
ord-b841cef548ae4bd8a946dd0b527e6a21
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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