Methanol → HCID 21098326, compound

To a solution of methyl 4-(bromomethyl)benzoate (5.00 g, 21.8 mmol) and acetone cyanohydrin (3 ml, 32.7 mmol) stirring at room temperature in acetonitrile (200 ml) was added 1,1,3,3-tetramethylguanidine (5.8 ml, 45.8 mmol) and the mixture stirred for 16 hours. The solvent was removed under reduced pressure. The residue was triturated with diethyl ether (×3), filtered and the filtrate evaporated under reduced pressure. The residue was purified by filtering through a pad of silica, eluting with diethyl ether to afford a colorless oil, 4.0 g. The oil was dissolved in 200 ml of diethyl ether and gaseous hydrogen chloride was bubbled though the solution until saturated while stirring at 0° C. Methanol (1.5 ml, 37.2 mmol) was added and the mixture stirred for 1 hour. The solvents were removed under reduced pressure and the residue was basified using saturated sodium carbonate solution and extracted with dichloromethane (×3). The combined organic solutions were dried (MgSO4), filtered and evaporated under reduced pressure to afford the title compound as a colourless oil, 4.20 g.

1. customThe solvent was removed under reduced pressure
2. customThe residue was triturated with diethyl ether (×3)
3. filtrationfiltered
4. customthe filtrate evaporated under reduced pressure
5. customThe residue was purified
6. filtrationby filtering through a pad of silica
7. washeluting with diethyl ether
8. customto afford a colorless oil, 4.0 g
9. customgaseous hydrogen chloride was bubbled though the solution until saturated
10. stirringwhile stirring at 0° C
11. stirringthe mixture stirred for 1 hour
12. customThe solvents were removed under reduced pressure
13. extractionextracted with dichloromethane (×3)
14. dry with materialThe combined organic solutions were dried (MgSO4)
15. filtrationfiltered
16. customevaporated under reduced pressure

ORD record

ord-aefcc6b409734355a12e837492b51d80

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07217714B1