Cyanogen Bromide → HCID 59323748, compound

Temperature

0 °C

To a stirred, cooled (0° C.) solution of (RS)-2-amino-2-(3-fluoro-2-methyl-phenyl)-ethanol (1.82 g) and sodium acetate (1.72 g) in methanol (17 ml) was added dropwise a solution of cyanogen bromide (1.18 g) in methanol (8 ml) over 10 min. The mixture was then stirred for 1 h at 0° C., then was allowed to warm to at r.t. and stirring continued for 2 h. The mixture was concentrated in vacuo and the residue was resuspended in water and made basic by addition of 1 M aq sodium hydroxide solution. The mixture was then extracted twice with dichloromethane and the combined organic phases were dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: dichloromethane/methanol) to give (RS)-4-(3-fluoro-2-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine (0.85 g, 41%) as a light yellow solid. MS (ISP): 195.3 ([M+H]+).

1. temperatureto warm to at r.t.
2. stirringstirring
3. waitcontinued for 2 h
4. concentrationThe mixture was concentrated in vacuo
5. additionmade basic by addition of 1 M aq sodium hydroxide solution
6. extractionThe mixture was then extracted twice with dichloromethane
7. dry with materialthe combined organic phases were dried over sodium sulphate
8. concentrationconcentrated in vacuo
9. customThe residue was purified by column chromatography (SiO2; gradient: dichloromethane/methanol)

ORD record

ord-67df041fb7244e8d98b9858273bfcc1a

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09132136B2