Nitrogen → 1-Azetidinebutanamine

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of trimethylene imine (300 mg, 5.25 mmol) and DBU (0.79 mL, 5.23 mmol) in dry Et2O (4 mL) was added 4-bromobutyronitrile (0.54 mL, 5.27 mmol) at 0° C. The reaction mixture was stirred at rt until completion of the reaction. The mixture was filtered and concentrated under reduced pressure. The crude nitrile was redissolved in dry THF (4 mL) and treated with LiALH4 (230 mg, 6.06 mmol) at 0° C. The reaction mixture was warmed up to rt and stirred at this temperature until completion of the reaction. Aq. 1N NaOH (2 mL) was then added, the layers separated and the aq. layer extracted with EA (3×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give crude 4-(azetidin-1-yl)butan-1-amine as a pale yellow oil. GC-MS-conditions 01: tR=1.35 min; [M+H]+=129.00.

1. filtrationThe mixture was filtered
2. concentrationconcentrated under reduced pressure
3. dissolutionThe crude nitrile was redissolved in dry THF (4 mL)
4. additiontreated with LiALH4 (230 mg, 6.06 mmol) at 0° C
5. temperatureThe reaction mixture was warmed up to rt
6. stirringstirred at this temperature until completion of the reaction
7. additionAq. 1N NaOH (2 mL) was then added
8. customthe layers separated
9. extractionthe aq. layer extracted with EA (3×)
10. washThe combined organic extracts were washed with brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. customthe solvents were removed under reduced pressure

ORD record

ord-163d9e6b41734e09b113d7dc09a0d01e

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563714B2