N,N-Dimethylethylenediamine → 2-(2-Dimethylamino-ethylamino)-cyclopent-1-enecarboxylic acid ethyl ester

HRID 731249Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=O)=[O:5])[CH3:2].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH2:16]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[NH:16][CH2:15][CH2:14][N:13]([CH3:17])[CH3:12])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-oxo-cyclopentanecarboxylic acid ethyl ester (5.00 g, 32.0 mmol) in ethanol (50 mL) was treated with N,N-dimethylethylenediamine (3.85 mL, 35.2 mmol). The solution was heated at reflux at 80° C. for 16 h. After cooling to 25° C. the solvent was removed in vacuo, and the residue was purified by flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0-100% ethyl acetate in hexanes) to afford the desired product, 2-(2-dimethylamino-ethylamino)-cyclopent-1-enecarboxylic acid ethyl ester (6.7 g, 29.6 mmol, 92.5%), as a light yellow oil. The product was used immediately in the following step without characterization.

Workup

temperatureThe solution was heated
temperatureAfter cooling to 25° C. the solvent
customwas removed in vacuo
customthe residue was purified by flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-ae2daaf8c01e4f0aa302a05e12f3a2a1
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582626B2

Reaction notes

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