CID 72256353 → racemic trans 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one

A catalyst solution was prepared by dissolving (R,R)-(+)-2,2′-bis[(S)—(N,N-dimethylamino)(phenyl)methyl]-1,1′-bis[di(3,5-dimethyl-4-methoxyphenyl)phosphino]ferrocene (52.6 mg; 0.05 mmol; identified above as Ligand Formula (A-1B)) and bis(1,5-cyclooctadiene)rhodium(I)tetrafluoroborate (20.4 mg; 0.05 mmol; also known as “Rh(COD)2BF4”) in dichloromethane (1 ml) under argon, and then stirring the resulting mixture at room temperature for 10 min. In parallel, 4,5-dihydro-imidazo[4,5,1-jk][1]benzazepin-2,6,7[1H]-trione-6-oxime (1.15 g, 5.0 mmol) was charged into a 100 mL autoclave and suspended in 40 mL of methanol. The autoclave was purged 3 times with H2 without stirring at 20 bar, and 3 times with stirring at 20 bar. Afterward, the catalyst solution, diluted with 4 ml of methanol, was charged into the autoclave. Hydrogen pressure (60 bar) was then applied, and the mixture was stirred at that pressure for 22 hr at 40° C. After cooling the mixture to room temperature and releasing the pressure, 2 g of Deloxan® THP II were added, and the resulting suspension was stirred at 55° C. for 10 min and filtered. The solvents were then removed to yield the product.

1. customA catalyst solution was prepared
2. customThe autoclave was purged 3 times with H2
3. stirringwithout stirring at 20 bar, and 3 times
4. stirringwith stirring at 20 bar
5. additionAfterward, the catalyst solution, diluted with 4 ml of methanol
6. additionwas charged into the autoclave
7. stirringthe mixture was stirred at that pressure for 22 hr at 40° C
8. temperatureAfter cooling the mixture to room temperature
9. additionwere added
10. stirringthe resulting suspension was stirred at 55° C. for 10 min
11. filtrationfiltered
12. customThe solvents were then removed
13. customto yield the product

ORD record

ord-06f233ff21bc45b387d9d102994abc82

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629134B2