1-Nonanol, 9-bromo- → (9-(9-Hydroxynonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Temperature

50 °C

9-Bromononan-1-ol (0.29 g) was added to a suspension of (2-methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone hydrochloride (example 1, step f) (0.4 g) in a mixture of triethylamine (0.41 mL) and acetonitrile (10 mL). The resulting mixture was stirred for 16 h at 50° C. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate (30 mL) and saturated sodium bicarbonate solution (30 mL). The layers were separated and the aqueous extracted with ethyl acetate (2×30 mL). The combined organic solutions were washed with brine (30 mL), dried over sodium sulphate, filtered and evaporated in vacuo. The residue was dissolved in methanol (10 mL) and applied to a SCX cartridge pre-wetted with methanol. The cartridge was washed with methanol (10 mL) and eluted with 3M ammonia in methanol solution (100 mL). The eluent was evaporated in vacuo to give the subtitled compound a yellow oil. Yield 0.32 g.

1. customThe solvent was evaporated in vacuo
2. customthe residue partitioned between ethyl acetate (30 mL) and saturated sodium bicarbonate solution (30 mL)
3. customThe layers were separated
4. extractionthe aqueous extracted with ethyl acetate (2×30 mL)
5. washThe combined organic solutions were washed with brine (30 mL)
6. dry with materialdried over sodium sulphate
7. filtrationfiltered
8. customevaporated in vacuo
9. dissolutionThe residue was dissolved in methanol (10 mL)
10. washThe cartridge was washed with methanol (10 mL)
11. washeluted with 3M ammonia in methanol solution (100 mL)
12. customThe eluent was evaporated in vacuo

ORD record

ord-fd9a60e9d0dd4b2eb8a148c43a4b4ca3

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148373B2