2-Benzofurancarboxaldehyde → HCID 68575168, Verbindung

Sodium triacetoxyborohydride (0.88 g, 4.16 mmol) is added to a stirred solution of 4-(3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.75 g, 2.77 mmol), benzofuran-2-carboxaldehyde (0.50 g, 3.46 mmol), and dichloromethane (14 ml). The reaction is stirred overnight at room temperature under nitrogen. The reaction is poured into aqueous saturated NaHCO3 (50 ml) and extracted with dichloromethane (25 ml×3). The organic layer is washed with aqueous saturated NaHCO3 and dried over Na2SO4, and filtered. The crude product is concentrated on a rotary evaporator and purified by flash chromatography on silica gel eluting with 0-30% (1:2 (10% NH4OH in methanol):ethanol) to yield (1.17 g) of 4-{[(benzofuran-2-yl)methyl]-(3-methylbutyl)-amino}-piperidine-1-carboxylic acid tert-butyl ester: mass spectrum (ion spray): m/z=401 (M+1); 1H NMR (CDCl3): δ=7.57-7.41 (2H, m), 7.30-7.16 (2H, m), 6.55 (1H, s), 4.15 (2H, brs), 3.81 (2H, s), 2.75-2.56 (6H, m), 1.80 (2H, brd), 1.63-1.53 (3H, m), 1.46 (9H, s), 1.42-1.33 (1H, m), 0.92-0.85 (6H, m).

1. extractionextracted with dichloromethane (25 ml×3)
2. washThe organic layer is washed with aqueous saturated NaHCO3
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationThe crude product is concentrated on a rotary evaporator
6. custompurified by flash chromatography on silica gel eluting with 0-30% (1:2 (10% NH4OH in methanol):ethanol)

ORD-Eintrag

ord-6e0c4636e2544f7c9137b0c59baf6d62

Quelldatensatz

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07521462B2