Methanol → 1-Oxa-2-azaspiro[4.5]dec-2-ene-3-carboxylic acid

Ethyl 1-oxa-2-aza-spiro[4.5]dec-2-ene-3-carboxylate (8.12 g, 38.5 mmol, as prepared in the previous step) was placed in a 200 mL round-bottom flask equipped with a magnetic stir bar, and MeOH (75 mL) and water (25 mL) were added. Lithium hydroxide monohydrate (1.77 g, 42.3 mmol) was added as a solid. The reaction was stirred at RT for 20 h, and the solvents were removed under reduced pressure. The resulting solid was triturated with ether and collected by filtration. The solid was then dissolved in water (200 mL) and acidified to pH 2 with 3 M aq HCl. The precipitate was isolated by filtration, washed well with water, air dried, and dried under vacuum. The filtrate was extracted three times with DCM (50 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure. The initial precipitate and the material from the extraction were combined, giving 5.81 g (83%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 2.93 (s, 2H), 1.72-1.89 (m, 4H), 1.60-1.72 (m, 2H), 1.37-1.54 (m, 4H).

1. customwas placed in a 200 mL round-bottom flask
2. customequipped with a magnetic stir bar
3. customthe solvents were removed under reduced pressure
4. customThe resulting solid was triturated with ether
5. filtrationcollected by filtration
6. dissolutionThe solid was then dissolved in water (200 mL)
7. customThe precipitate was isolated by filtration
8. washwashed well with water, air
9. customdried
10. customdried under vacuum
11. extractionThe filtrate was extracted three times with DCM (50 mL)
12. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
13. filtrationfiltered
14. customthe solvent was removed under reduced pressure
15. extractionThe initial precipitate and the material from the extraction

ORD-Eintrag

ord-c5490b4f6a51432185c56e2b8588e245

Quelldatensatz

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08232409B2