Potassium Carbonate → Isoguvacine

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).

1. customthe phases were separated
2. customThe aqueous layer was dried under reduced pressure
3. customthe residue was triturated with dichloromethane (100×3 mL)
4. dissolutiondissolved in methanol (100 mL)
5. concentrationthe mixture was concentrated under reduced pressure
6. customThe residue was triturated with methanol (200×5 mL)
7. customdried under reduced pressure

ORD record

ord-2305a52d14f44b408e76d21fa2557c2f

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129235B2