ethyl 1,2,3,6-tetrahydropyridine-4-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl 1,2,3,6-tetrahydro-4-pyridinecarboxylate (44.7 g, 234 mmol) in dichloromethane (200 mL) was treated with aqueous K2CO3 (saturated) and the phases were separated. The aqueous layer was dried under reduced pressure and the residue was triturated with dichloromethane (100×3 mL) and dissolved in methanol (100 mL). The solution was treated with a saturated solution of NaOH (10 g, 250 mmol) in methanol (250 mL) and sodium methoxide in methanol (0.5M, 200 mL, 100 mmol). After stirring at room temperature for two days, the mixture was concentrated under reduced pressure. The residue was triturated with methanol (200×5 mL) and dried under reduced pressure to provide the title compound. 1H NMR (300 MHz, CD3OD) δ 6.60 (m, 1H), 3.38 (m, 2H), 2.88 (m, 2H), 2.30 (m, 2H). the phases were separated The aqueous layer was dried under reduced pressure the residue was triturated with dichloromethane (100×3 mL) dissolved in methanol (100 mL) the mixture was concentrated under reduced pressure The residue was triturated with methanol (200×5 mL) dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(1-Chloroethyl) 4-ethyl 3,6-dihydro-1,4(2H)-pyridinedicarboxylate (61.8 g, 236 mmol) in methanol (500 mL) was heated at reflux for 30 minutes. The mixture was allowed to cool to room temperature and concentrated to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 6.86 (m, 1H), 4.22 (q, 2H), 3.85 (m, 2H), 3.34 (m, 2H), 2.75 (m, 2H), 1.30 (t, 3H). at reflux for 30 minutes concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl 1,2,3,6-tetrahydro-4-pyridinecarboxylate (44.7 g, 234 mmol) in dichloromethane (200 mL) was treated with aqueous K2CO3 (saturated) and the phases were separated. The aqueous layer was dried under reduced pressure and the residue was triturated with dichloromethane (100×3 mL) and dissolved in methanol (100 mL). The solution was treated with a saturated solution of NaOH (10 g, 250 mmol) in methanol (250 mL) and sodium methoxide in methanol (0.5M, 200 mL, 100 mmol). After stirring at room temperature for two days, the mixture was concentrated under reduced pressure. The residue was triturated with methanol (200×5 mL) and dried under reduced pressure to provide the title compound. 1H NMR (300 MHz, CD3OD) δ 6.60 (m, 1H), 3.38 (m, 2H), 2.88 (m, 2H), 2.30 (m, 2H). the phases were separated The aqueous layer was dried under reduced pressure the residue was triturated with dichloromethane (100×3 mL) dissolved in methanol (100 mL) the mixture was concentrated under reduced pressure The residue was triturated with methanol (200×5 mL) dried under reduced pressure