Aluminium lithium hydride → 2-(2-Tert-butoxyphenyl)ethanamine

Temperature

0 °C

1-tert-Butoxy-2-(2-nitrovinyl)benzene (685 mg, 3.10 mmol) in tetrahydrofuran (10 ml) was cooled to 0° C. under an argon atmosphere (balloon). Lithium aluminum hydride (1 M in THF) (12384 μL, 12.4 mmol, equivalent to 470 mg) was added dropwise over 5 minutes. The reaction was stirred at 0° C. for 30 minutes and then at ambient temperature 4 hours. The reaction was quenched with 0.470 ml water at 0° C., followed by 0.470 ml 1 N aqueous NaOH at 0° C. After 15 minutes, an additional 1.45 ml water was added and the reaction mixture was warmed to ambient temperature and stirred rapidly for 1 hour, after which ethyl acetate (20 ml) and potassium were added. The reaction mixture was filtered and washed with ethyl acetate. The combined filtrate was concentrated in vacuo to afford the title compound (575 mg, 2.97 mmol, 96.1% yield) as a yellow oil.

1. customat ambient temperature
2. custom4 hours
3. customThe reaction was quenched with 0.470 ml water at 0° C.
4. customfollowed by 0.470 ml 1 N aqueous NaOH at 0° C
5. waitAfter 15 minutes
6. additionan additional 1.45 ml water was added
7. temperaturethe reaction mixture was warmed to ambient temperature
8. stirringstirred rapidly for 1 hour
9. additionafter which ethyl acetate (20 ml) and potassium were added
10. filtrationThe reaction mixture was filtered
11. washwashed with ethyl acetate
12. concentrationThe combined filtrate was concentrated in vacuo

ORD record

ord-46164824f7cd4f91b0e9070ba7e383ea

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716498B2