Aluminium lithium hydride → 3,3-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepine

A suspension of 7-bromo-3,3-dimethyl-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-one (0.50 g, 1.8 mmol) in THF (15 mL) was cooled in an ice bath and treated dropwise with LiAlH4 (4.1 mL of a 1.0 M solution in THF, 4.1 mmol). After stirring for 30 mm, the ice bath was removed and the solution was allowed to warm to room temperature. After heating to reflux overnight, the mixture was cooled in an ice bath. The reaction was quenched sequentially with H2O (0.15 mL), 15% NaOH (0.15 mL) and H2O (0.45 ml). After 5 min, the ice bath was removed and the mixture was stirred at room temperature for 1.5 h. The mixture was filtered through Celite, and the filtrate was concentrated in vacuo to give the title compound (0.43 g; quantitative) as a white solid; 1H NMR (300 MHz, CDCl3) δ7.90 (dd, J=4.9, 1.5 Hz, 1H), 7.17 (d, J=7.2 Hz, 1H), 6.61 (dd, J=7.2, 4.9 Hz, 1H), 4.85 (br s, 1H), 3.91 (s, 2H), 3.22 (d, J=4.5 Hz, 2H), 2.39 (br s, 1H), 1.20 (s, 6H); MS (ESI) m/e 178 (M+H)+.

1. temperaturewas cooled in an ice bath
2. customthe ice bath was removed
3. temperatureAfter heating
4. temperatureto reflux overnight
5. temperaturethe mixture was cooled in an ice bath
6. customThe reaction was quenched sequentially with H2O (0.15 mL), 15% NaOH (0.15 mL) and H2O (0.45 ml)
7. customthe ice bath was removed
8. stirringthe mixture was stirred at room temperature for 1.5 h
9. filtrationThe mixture was filtered through Celite
10. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-4a6a5d2bc4bf41639e31e8f55997d512

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895545B2