Water → 2,2,2-Trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate

Temperature

0 °C

A solution of trifluoroacetic anhydride (9.6 mL) in DCM (10 mL) was added dropwise, over a period of 15 minutes, to a stirred solution of triethylamine (15.2 mL) and tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride [WuXi PharmaTech] (9.95 g) in DCM (100 mL) at 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 30 minutes. More triethylamine (2.5 mL) was added, followed by more trifluoroacetic anhydride (1.6 mL) in DCM (10 mL), and stirring at 0° C. was continued for 1 hour. Water (100 mL) was added and the mixture was vigorously stirred for 10 minutes. The organic layer was separated, dried, and the solvent evaporated under reduced pressure. The residue was dissolved in DCM (100 mL) and the solution treated with trifluoroacetic acid (25 mL). This mixture was allowed to stand at 20° C. for 10 minutes and then diluted with toluene (40 mL). The solvents were removed under reduced pressure and the residue azeotroped with more toluene (×2) to yield the subtitled compound. Yield 14.0 g.

1. stirringstirring at 0° C.
2. waitwas continued for 1 hour
3. stirringthe mixture was vigorously stirred for 10 minutes
4. customThe organic layer was separated
5. customdried
6. customthe solvent evaporated under reduced pressure
7. dissolutionThe residue was dissolved in DCM (100 mL)
8. additionthe solution treated with trifluoroacetic acid (25 mL)
9. waitto stand at 20° C. for 10 minutes
10. additiondiluted with toluene (40 mL)
11. customThe solvents were removed under reduced pressure
12. customthe residue azeotroped with more toluene (×2)

ORD record

ord-4daff82a89614f6f97ba3096cee5bd5d

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476265B2