1-AZASPIRO[4.5]DECANE-2,8-DIONE

To a stuffed solution of the above methyl 8-hydroxy-2-1-azaspiro (4, 5) dec-7-ene- 7-carboxylate (22 g 97.77 mmol) in methamol (200 ml) at room temperature was added aqueous 4 N NaOH (7.82 g, 195.5 mmol). The reaction mixture was stirred at 100 C for 3.5 h. After the reaction mixture was cooled to room temperature the mixture was carefully neutralized with acetic acid. The solvent was removed under reduced pressure and the resulting crude product was used in the next reaction without further purification. 'H-NMR (400 MHz, CDC13) & 8.49 (brs, 1H), 2.63-2.39 (m, 6H), 1.94-2.11 (m, 6H).To a stuffed solution of the 1-azaspiro-(4, 5)-dec-2, 8-dione (8 g 47.9 mmol) in toluene (120 ml) at room temperature was added PTSA (0.91 g, 0.47 mmol) and ethylene glycol (9.3 ml, 167 mmol). The reaction mixture was stuffed at 120 C for 2.5 h in Dean-Stark assembly. After the reaction mixture was cooled to room temperature and extracted in ethyl acetate (3x 150 ml), dried over sodium sulphate and concentrated under reduced pressure and the resulting crude purified by column chromatography to give title compound (84.1%). 'HNMR (400 MHz, CDC13) & 6.86 (s, 1H), 3.93 (s, 4H), 2.39-2.43 (q, 2H), 1.97 (t, 2H), 1.81- 1.68 (m, 8H). LCMS: mlz=212 [M+1].

Molecular Weight:167.20
XLogP3:-0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:167.094628657
Monoisotopic Mass:167.094628657
Topological Polar Surface Area:46.2
Heavy Atom Count:12
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes