Sodium Hydroxide → 5-bromo-3-methyl-1'-(tetrahydro-2H-pyran-4-yl)-1',2',3',6'-tetrahydro-2,4'-bipyridine

Sodium triacetoxyborohydride (5.25 g) was added at room temperature to a solutions of 5-bromo-3-methyl-1′,2′,3′,6′-tetrahydro-2,4′-bipyridine (5.23 g) and tetrahydro-4H-pyran-4-one (2.07 g) in tetrahydrofuran (50 ml) and n-hexane (20 ml), and stirred at the same temperature. After completion of the reaction, 1N aqueous solution of sodium hydroxide was added under ice cooling and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chloroform/methanol) and washed with diethyl ether and n-hexane to give 5-bromo-3-methyl-1′-(tetrahydro-2H-pyran-4-yl)-1′,2′,3′,6′-tetrahydro-2,4′-bipyridine (3.1 g) as a pale yellow solid.

1. additionwas added under ice cooling
2. extractionextracted with chloroform
3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
4. concentrationconcentrated
5. customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol)
6. washwashed with diethyl ether and n-hexane

ORD-Eintrag

ord-aeb14af93d084ea5b67d2ec9ba2d2ef4

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09150555B2