Propylamine → N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)propan-1-amine

To a solution of propylamine (0.72 mL, 7.7 mmol) and 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1.0 g, 7.7 mmol) in 1,2-dichloroethane (25 mL) was added sodium triacetoxyborohydride (2.28 g, 10.8 mmol). The mixture was stirred for 1.5 h at room temperature. The reaction mixture was then quenched with sat'd aq NaHCO3 and extracted with EtOAc. The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient) to afford 1.26 g (73%) of N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)propan-1-amine.

1. customThe reaction mixture was then quenched with sat'd aq NaHCO3
2. extractionextracted with EtOAc
3. dry with materialThe organic layer was dried with MgSO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customto give the crude material that
7. customwas purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient)

ORD record

ord-a8eb68fa38d04981945bcca9a25c70a9

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242964B2