Tetrabutylammonium Fluoride → (9-((5-(2-Hydroxyethyl)thiophen-3-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Tetrabutylammonium fluoride (1M in tetrahydrofuran, 2.1 mL) was added to a solution of (9-((5-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-3-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 278, step d) (0.80 g) in tetrahydrofuran (10 mL). After 2 h, the solution was evaporated in vacuo and the residue partitioned between saturated sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×50 mL). The combined organic solutions were washed with brine (50 mL), dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography, eluting with 20:1 ethyl acetate:triethylamine. The fractions containing product were combined and evaporated in vacuo to give the subtitled compound as a gum. Yield 0.61 g.

1. customthe solution was evaporated in vacuo
2. customthe residue partitioned between saturated sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL)
3. customThe layers were separated
4. extractionthe aqueous phase extracted with ethyl acetate (2×50 mL)
5. washThe combined organic solutions were washed with brine (50 mL)
6. dry with materialdried over sodium sulphate
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by silica gel chromatography
10. washeluting with 20:1 ethyl acetate
11. additionThe fractions containing product
12. customevaporated in vacuo

ORD record

ord-02feb54e2d61468f8843592a64a3bca3

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2