Sodium sulfate decahydrate → 1-Methyl-1,2,3,6-tetrahydropyridine-4-carboaldehyde

To a solution prepared by dissolving 1.7 g of ethyl 1-methyl-1,2,3,6-tetrahydro-4-pyridinecarboxylate in 20 mL of tetrahydrofuran, 773 mg of lithium aluminum hydride was added, and the mixture was stirred for 1 hour at room temperature. The reaction solution was cooled to 0° C., and then sodium sulfate decahydrate was slowly added until there are no bubbles, and stirred overnight at room temperature. The insolubles were filtered and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in 40 mL of chloroform, then 2 g of manganese dioxide was added thereto, and the mixture was stirred overnight at room temperature. The insolubles were filtered through celite, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0-90/10), to obtain 212 mg of 1-methyl-1,2,3,6-tetrahydropyridine-4-carboaldehyde [34-1] (hereinafter, referred to as the compound [34-1]).

1. customTo a solution prepared
2. additionwas added
3. temperatureThe reaction solution was cooled to 0° C.
4. stirringstirred overnight at room temperature
5. filtrationThe insolubles were filtered
6. concentrationthe filtrate was concentrated under reduced pressure
7. dissolutionThe obtained residue was dissolved in 40 mL of chloroform
8. addition2 g of manganese dioxide was added
9. stirringthe mixture was stirred overnight at room temperature
10. filtrationThe insolubles were filtered through celite
11. concentrationthe filtrate was concentrated under reduced pressure
12. customthe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0-90/10)

ORD record

ord-ba6e10397bc04c8dac1a6db9689c18cb

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977336B2