反应详情

3-(2-Hydroxyethylthio)benzaldehyde (example 65, step c) (0.16 g) was added to a solution of (2-isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 22, step b) (0.25 g) and acetic acid (0.046 mL) in N-methyl-2-pyrrolidinone (5 mL) and the resulting mixture was stirred for 1 h and cooled in an ice bath. Sodium triacetoxyborohydride (0.26 g) was then added and the mixture allowed to warm to RT and stirred overnight. The reaction was poured into a mixture of sodium bicarbonate solution (20 mL) and water (80 mL). The aqueous phase was extracted with ether (3×100 mL). The combined organic solutions were washed with brine (100 mL), dried over sodium sulphate, filtered and evaporated. The crude product was purified by silica gel chromatography eluting with 95:5 ethyl acetate:triethylamine. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 0.22 g.

1. temperaturecooled in an ice bath
2. stirringstirred overnight
3. extractionThe aqueous phase was extracted with ether (3×100 mL)
4. washThe combined organic solutions were washed with brine (100 mL)
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. customevaporated
8. customThe crude product was purified by silica gel chromatography
9. washeluting with 95:5 ethyl acetate
10. additionThe fractions containing product
11. customevaporated