Ethyl Acetate → Diethyl [3-(4-aminophenyl)propyl]malonate

HRID 1713861Notes

Reaction equation

HRID 1713861 reaction equation
[NH2:1]C1C=CC(C2CCC(C(OC)=O)C2)=CC=1.[C:17]1([CH2:23][CH2:24][CH2:25][CH:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCOC(C)=O>CCO>[NH2:1][C:20]1[CH:19]=[CH:18][C:17]([CH2:23][CH2:24][CH2:25][CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 106363121,3-Diethyl 2-(3-phenylpropyl)propanedioateHCID 59464327Methyl 3-(4-aminophenyl)cyclopentanecarboxylate

Product 1

HCID 59464339Diethyl [3-(4-aminophenyl)propyl]malonateYield 10%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the general procedure of Intermediate 84 except that diethyl (3-phenylpropyl)malonate (J. Med. Chem., 2004, 47(12), 3282) was used in place of methyl 3-phenylcyclopentanecarboxylate, nitration and reduction (using EtOAc as solvent in place of EtOH) gave the title compound (purified by chromatography, eluting with 10-50% EtOAc/Isohexane); 1H NMR δ 1.17 (t, 6H), 1.42-1.53 (m, 2H), 1.69-1.78 (m, 2H), 2.40 (t, 2H), 3.45 (t, 1H), 4.07-4.16 (m, 4H), 4.81 (s, 2H), 6.48 (d, 2H), 6.81 (d, 2H); MS m/e MH+ 294.

Sources & evidence

ORD record
ord-47ed4103c7604b158810ad7744110f0c
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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