Aluminium lithium hydride → 1,1-Cyclobutanedimethanamine, 3,3-difluoro-

Temperature

0 °C

To a cooled solution of 3,3-difluorocyclobutane-1,1-dicarboxamide (1.858 g, 10.4 mmol) in tetrahydrofuran (25 mL) at −10° C., was added slowly lithium aluminium hydride (2.375 g, 62.58 mmol). The reaction was stirred at 0° C. for 4 hours and then heated under reflux for 30 hours. The mixture was cooled and quenched at 0° C. by addition of water (2.5 mL), 15% aqueous solution of sodium hydroxide (7.5 mL) and water (2.5 mL) successively. The resulting mixture was stirred at room temperature for 0.5 hour. The mixture was filtered and the filtrate was concentrated in vacuo to afford 1.137 g of the crude product of (3,3-difluorocyclobutane-1,1-diyl)dimethanamine as a colorless oil (yield was 72.8%).

1. temperatureheated
2. temperatureunder reflux for 30 hours
3. temperatureThe mixture was cooled
4. customquenched at 0° C. by addition of water (2.5 mL), 15% aqueous solution of sodium hydroxide (7.5 mL) and water (2.5 mL) successively
5. stirringThe resulting mixture was stirred at room temperature for 0.5 hour
6. filtrationThe mixture was filtered
7. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-74cca238b72145bc9e7038f41bb5a51e

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871756B2