Aluminium lithium hydride → tert-Butyl 3-(aminomethyl)-3-fluoropiperidine-1-carboxylate

To a stirred and cooled (0° C.) suspension of lithium aluminium hydride (1.02 g, 26.8 mmol) in dry THF (50 mL) was added drop-wise a solution of tert-butyl 3-cyano-3-fluoropiperidine-1-carboxylate (5.50 g, 24.0 mmol) in dry THF (30 mL). The reaction was stirred at 0° C. for 1 hour then at room temperature for 3 hours. The mixture was quenched with water (1.0 mL) at 0° C., and stirred at room temperature for 20 minutes. Then 15% sodium hydroxide aqueous solution (2.0 mL) was added, and stirred at room temperature for 20 minutes. Finally, water (1.0 mL) was added, and stirred at room temperature for 20 minutes. The mixture was filtered through Celite pad washing with tetrahydrofuran (25 mL). The filtrate was concentrated to afford the title product as pale yellow oil 3.86 g. MS (m/z): 233 (M+H)+

1. temperaturecooled
2. stirringThe reaction was stirred at 0° C. for 1 hour
3. customThe mixture was quenched with water (1.0 mL) at 0° C.
4. stirringstirred at room temperature for 20 minutes
5. additionThen 15% sodium hydroxide aqueous solution (2.0 mL) was added
6. stirringstirred at room temperature for 20 minutes
7. additionFinally, water (1.0 mL) was added
8. stirringstirred at room temperature for 20 minutes
9. filtrationThe mixture was filtered through Celite pad
10. washwashing with tetrahydrofuran (25 mL)
11. concentrationThe filtrate was concentrated

ORD record

ord-eb2e37702fad498aad58d7c95909946a

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434726B2