Diethyl acetonedicarboxylate → Diethyl 3-cyclopropylamino-2-pentenedioate

HRID 1649692Notes

Reaction equation

HRID 1649692 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)=[O:5].[CH:15]1([NH2:18])[CH2:17][CH2:16]1>O>[CH:15]1([NH:18][C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 66045Diethyl acetonedicarboxylateHCID 69828Cyclopropylamine

Product 1

HCID 67931504Diethyl 3-cyclopropylamino-2-pentenedioateYield 95.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30.33 g (0.15 mol) of diethyl acetonedicarboxylate was added dropwise 11.8 g (0.19 mol) of cyclopropylamine at such a rate that reaction temperature was kept below 48° C. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into H2O, extracted twice with ether, dried (MgSO4) and concentrated in vacuo affording 34.42 g of a light yellow oil. Crude was kugelrohr distilled at 53 Pa and collected at a pot temperature of 102°-104° C. to give 23.73 g (66%) of enamine diester as a light yellow oil, nD25 1.5025.

Workup

  1. customthat reaction temperature
  2. customwas kept below 48° C
  3. extractionextracted twice with ether
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c4073265f8f456dbd371d1de3a3cf9a
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Reaction notes

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