Beta-Alanine → 2-Isobutylsuccinic acid-4-t-butyl ester-1-methyl ester

HRID 1167956Notes

Reaction equation

HRID 1167956 reaction equation
C(C[C:4](OCC)=[O:5])#N.[C:9]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.C1C[CH2:19][C:18](CN)([CH2:21]C(O)=O)[CH2:17]C1.NC[CH2:29][C:30]([OH:32])=[O:31].[C:33]([O-])(=O)C.[NH4+].N1CCCCC1>O.C(O)(=O)C.CCCCCCC.C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:4][O:5][C:9](=[O:14])[CH:13]([CH2:12][CH:11]([CH3:10])[CH3:33])[CH2:29][C:30]([O:32][C:18]([CH3:21])([CH3:19])[CH3:17])=[O:31]

Participants

12

Reactant 6

HCID 239Beta-AlanineHCID 3446GabapentinHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 8452CyclopentanoneHCID 517165Ammonium Acetate

Product 1

HCID 218883142-Isobutylsuccinic acid-4-t-butyl ester-1-methyl ester

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

An alkyl cyanoacetate, for example ethyl cyanoacetate, is added to a mixture of cyclopentanone of formula (1) in a solvent selected from toluene, benzene, xylenes, or n-heptane to which acetic acid and β-alanine or ammonium acetate, or piperidine are added. The mixture is stirred at a temperature from 0° C. to 150° C. with removal of water by, for example, use of a Dean-Stark trap or activated molecular sieves, to produce the alkene of formula (2);

Workup

  1. additionare added

Sources & evidence

ORD record
ord-72aac80cfe8b46c78c94c4e41425ab9e
Source dataset
uspto-grants-2003_09
Patent number
US06620829B2

Reaction notes

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