Ethyl Acetoacetate → 1-(1-Ethoxycarbonyl-2-prop-1-enylamino)-2-(1-ethoxycarbonyl-2-prop-1-enylaminomethyl)-3,3,5-trimethylcyclopentane

HRID 1060206Notes

Reaction equation

HRID 1060206 reaction equation
[NH2:1][CH:2]1[CH:6]([CH2:7][NH2:8])[C:5]([CH3:10])([CH3:9])[CH2:4][CH:3]1[CH3:11].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=O>CO>[CH2:19]([O:18][C:12]([CH:13]=[C:14]([NH:1][CH:2]1[CH:3]([CH3:11])[CH2:4][C:5]([CH3:10])([CH3:9])[CH:6]1[CH:7]([NH:8][C:14]([CH3:16])=[CH2:13])[C:12]([O:18][CH2:19][CH3:20])=[O:17])[CH3:16])=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 106962Cyclopentanemethanamine, 5-amino-2,2,4-trimethyl-

Product 1

HCID 698583841-(1-Ethoxycarbonyl-2-prop-1-enylamino)-2-(1-ethoxycarbonyl-2-prop-1-enylaminomethyl)-3,3,5-trimethylcyclopentaneYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To 5-amino-2,2,4-trimethylcyclopentylmethylamine (127.76 g, 0.819 mol) in methanol (700 ml) was slowly added with stirring ethyl acetoacetate (215.85 g, 1.660 mol) in methanol (700 ml) over 35 minutes, during which the temperature increased from 22° C. to 31° C. The reaction mixture was allowed to stand at 21° C. overnight (17 h). Further methanol was added, and removal of solvent and drying (91°/100 Pa) gave 1-(1-ethoxycarbonyl-2-prop-1-enylamino)-2-(1-ethoxycarbonyl-2-prop-1-enylaminomethyl)-3,3,5-trimethylcyclopentane (EEMTCP, formula shown below) as a clear light yellow pourable viscous oil (296.54 g, 95%) identified by 1H-NMR, 13C-NMR, FT-IR and Raman spectra.

Workup

  1. temperatureincreased from 22° C. to 31° C
  2. custom(17 h)
  3. customremoval of solvent
  4. customdrying (91°/100 Pa)

Sources & evidence

ORD record
ord-89e0d59b2655480b9e0ffffefc1775c7
Source dataset
uspto-grants-2003_02
Patent number
US06521716B1

Reaction notes

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