ethyl 6-aminohexanoate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of ε-aminocaproic acid (70.0 g, 533.8 mmol), toluenesulfonic acid (111.7 g, 1.1 eq.) and ethanol (1.6 L) was heated to reflux for 20 hours. Thereafter, TLC (CH2Cl2/EtOH/TEA, 85:10:5) revealed complete conversion. The reaction mixture was concentrated until solids started to precipitate. The precipitation was driven to completion by adding diethyl ether (1.5 L). The white solid was filtered, washed with diethyl ether, and dried in vacuo affording 174.0 g (98.3%) of a white powder. 1H NMR: (200 MHz, CDCl3): δ 7.47 (d, 2H, J=8.2 Hz), 7.10 (d, 2H, J=8.2 Hz), 4.02 (q, J=7.0 Hz), 2.79-2.65 (m, 2H), 2.28 (s, 3H), 2.25 (t, 2H, J=7.0 Hz), 1.16 (t, 3H, J=7.0 Hz), 1.49 (dt, 4H, J=7.6, 7.0 Hz), 1.29-1.22 (m, 2H). 13C NMR: 173.4, 145.6, 138.8, 128.9, 126.1, 60.4, 39.4, 33.9, 27.3, 25.9, 24.6, 21.5, 14.8. was heated to reflux for 20 hours The reaction mixture was concentrated until solids to precipitate The precipitation by adding diethyl ether (1.5 L) The white solid was filtered washed with diethyl ether dried in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 196 mg of ethyl nicotinoylacetate and 192 mg of ethyl 6-aminocaproate is heated at 120°-130° under nitrogen for 18 hours. The product is purified by preparative TLC (silica gel; chloroform, ethyl acetate 9.1) to yield ethyl β-(3-pyridyl)-β-(5-ethoxycarbonylpentylamino)acrylate;Rf =0.3. is heated at 120°-130° under nitrogen for 18 hours The product is purified by preparative TLC (silica gel; chloroform, ethyl acetate 9.1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of ε-aminocaproic acid (70.0 g, 533.8 mmol), toluenesulfonic acid (111.7 g, 1.1 eq.) and ethanol (1.6 L) was heated to reflux for 20 hours. Thereafter, TLC (CH2Cl2/EtOH/TEA, 85:10:5) revealed complete conversion. The reaction mixture was concentrated until solids started to precipitate. The precipitation was driven to completion by adding diethyl ether (1.5 L). The white solid was filtered, washed with diethyl ether, and dried in vacuo affording 174.0 g (98.3%) of a white powder. 1H NMR: (200 MHz, CDCl3): δ 7.47 (d, 2H, J=8.2 Hz), 7.10 (d, 2H, J=8.2 Hz), 4.02 (q, J=7.0 Hz), 2.79-2.65 (m, 2H), 2.28 (s, 3H), 2.25 (t, 2H, J=7.0 Hz), 1.16 (t, 3H, J=7.0 Hz), 1.49 (dt, 4H, J=7.6, 7.0 Hz), 1.29-1.22 (m, 2H). 13C NMR: 173.4, 145.6, 138.8, 128.9, 126.1, 60.4, 39.4, 33.9, 27.3, 25.9, 24.6, 21.5, 14.8. was heated to reflux for 20 hours The reaction mixture was concentrated until solids to precipitate The precipitation by adding diethyl ether (1.5 L) The white solid was filtered washed with diethyl ether dried in vacuo