Cyanogen Bromide → HCID 86626151, compound

To a 50 ml round-bottom flask containing a solution of lysergic acid methyl ester (1.0 g, 3.54 mmol) in anhydrous dichloromethane (50 ml) is slowly added cyanogen bromide (2.02 g, 19.11 mmol) and the resulting black-coloured reaction mixture is stirred at room temperature for 4 hours by which time TLC in 10% methanol/dichloromethane showed partial conversion of starting material to give two faster-running products. The reaction mixture is left stirring over the weekend and monitored by TLC showing no change. The reaction mixture is then stirred at 50° C. for 4 hours and is then extracted between tartaric acid and dichloromethane. The aqueous phase is re-extracted with dichloromethane (100 ml) and the combined organic phases washed with brine (200 ml), dried over MgSO4, filtered and concentrated in vacuo to give a dark brown (tar-coloured) oil. Purification is carried out by Normal Phase Flash column chromatography (Biotage Flash 40, 90 g cartridge) using 40% ethyl acetate/hexane to achieve separation of the fast-running product which is isolated as a pale yellow solid. The product is crystallized from tert. Butyl methylether and slowly evaporated. The resulting crystallized material is filtered at the pump to give pale yellow crystals.

1. customto give two faster-running products
2. waitThe reaction mixture is left
3. stirringThe reaction mixture is then stirred at 50° C. for 4 hours
4. extractionis then extracted between tartaric acid and dichloromethane
5. extractionThe aqueous phase is re-extracted with dichloromethane (100 ml)
6. washthe combined organic phases washed with brine (200 ml)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a dark brown (tar-coloured) oil
11. customPurification
12. customseparation of the fast-running product which
13. customis isolated as a pale yellow solid
14. customThe product is crystallized from tert. Butyl methylether
15. customslowly evaporated
16. customThe resulting crystallized material
17. filtrationis filtered at the pump
18. customto give pale yellow crystals

ORD record

ord-1d3d38b576774ca890601bf57d535211

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07666877B2