1,5-Diazabicyclo(4.3.0)non-5-ene → HCID 53911394, compound

The product of step (ii) (22.8 g). 3-bromobenzaldehyde (4.5 ml) and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) (5.95 g) in acetonitrile (50 ml) was heated under reflux for 0.5 hours. The solution was evaporated under reduced pressure. The residue was dissolved in dichloromethane, washed with 2M HCl, dried (MgSO4) and evaporated. The residue and potassium hydroxide (5.6 g) in water (100 ml) and methanol (20 ml) was heated under reflux for 8 hours. The reaction mixture was diluted with water and washed with dichloromethane. The aqueous solution was acidified to pH 1 (2N HCl) and extracted with dichloromethane. The organic solution was dried (MgSO4), evaporated and the product purified by chromatography eluting with toluene. Yield 8.5 g. Used directly in the next step.

1. temperatureunder reflux for 0.5 hours
2. customThe solution was evaporated under reduced pressure
3. dissolutionThe residue was dissolved in dichloromethane
4. washwashed with 2M HCl
5. dry with materialdried (MgSO4)
6. customevaporated
7. temperatureThe residue and potassium hydroxide (5.6 g) in water (100 ml) and methanol (20 ml) was heated
8. temperatureunder reflux for 8 hours
9. additionThe reaction mixture was diluted with water
10. washwashed with dichloromethane
11. extractionextracted with dichloromethane
12. dry with materialThe organic solution was dried (MgSO4)
13. customevaporated
14. customthe product purified by chromatography
15. washeluting with toluene

ORD record

ord-59d05087ac5b4154a978e70b2ff957c0

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06162808