Acetic Acid → n-((2-Bromo(3-pyridyl))methyl)-2-(1,3-dioxolan-2-yl)ethylamine

To a solution of 2-bromopyridine-3-carbaldehyde (3.53 g, 19.0 mmol, 1.0 eq) (Melnyk et al., Synthetic Commun. 23(19):2727-2730, 1993) in 1,2-dichloroethane (50 mL) was added 2-(1,3-dioxolan-2-yl)ethylamine (TCI-GR, 2.67 g, 22.8 mmol, 1.2 eq), sodium triacetoxyborohydride (Aldrich, 1.61 g, 76 mmol, 4.0 eq) and glacial acetic acid (1.14 g, 19 mmol, 1.0 eq). The reaction mixture was stirred under nitrogen at room temperature for 2 h. The reaction was quenched with 1.0 N aqueous NaOH to about pH 8 and the solution was extracted with EtOAc (200 mL×3). The organic extracts were washed with saturated NaCl, dried with MgSO4, filtered and concentrated. Flash column chromatography (silica gel, 0-10% EtOAc-Hexane) afforded the title compound as a colorless oil. MS m/z 377 (Br=79, M+H), 379 (Br=81, M+H).

1. customThe reaction was quenched with 1.0 N aqueous NaOH to about pH 8
2. extractionthe solution was extracted with EtOAc (200 mL×3)
3. washThe organic extracts were washed with saturated NaCl
4. dry with materialdried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated

ORD-Eintrag

ord-1a0522ab9a454381afebffe8fe1e703b

Quelldatensatz

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06514964B1