| Identification | Back Directory | [Name]
TERT-BUTYL 3-OXO-2,8-DIAZASPIRO[4.5]DECANE-8-CARBOXYLATE | [CAS]
169206-67-1 | [Synonyms]
SW-90
SWF-90
8-Boc-3-oxo-2,8-diazaspir...
8-Boc-2,8-diazaspiro[4.5]decan-3-one
8-Boc-3-oxo-2,8-diazaspiro[4.5]decane
TERT-BUTYL 3-OXO-2,8-DIAZASPIRO[4.5]DECANE-8-CARBOXYLATE
tert-Butyl 2-oxo-3,8-diazaspiro[4.5]decane-8-carboxylate
2,8-diazaspiro[4.5]decane-8-carboxylic acid, 3-oxo-, 1,1-d
3-keto-2,8-diazaspiro[4.5]decane-8-carboxylic acid tert-butyl ester
2,8-Diazaspiro[4.5]decane-8-carboxylic acid,3-oxo-,1,1-diMethylethyl ester | [Molecular Formula]
C13H22N2O3 | [MDL Number]
MFCD11111226 | [MOL File]
169206-67-1.mol | [Molecular Weight]
254.33 |
| Chemical Properties | Back Directory | [Boiling point ]
425℃ | [density ]
1.15 | [Fp ]
211℃ | [storage temp. ]
Sealed in dry,2-8°C | [pka]
16.26±0.20(Predicted) | [Appearance]
White to light yellow Solid |
| Hazard Information | Back Directory | [Uses]
Tert-butyl 3-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate is an organic heterocyclic compound used as a pharmaceutical intermediate. It is used in the synthesis of growth inhibitor receptor 5 (SSTR5) antagonists for the treatment of conditions involving the gut-brain axis. | [Synthesis]
General procedure for the synthesis of tert-butyl 3-oxo-2,8-diazaspiro[4,5]decane-8-carboxylate from tert-butyl 4-(2-methoxy-2-oxoethyl)-4-(nitromethyl)piperidine-1-carboxylate: To a tert-butyl 4-(2-methoxy-2-oxoethyl)-4-(nitromethyl)piperidine-1-carboxylate (1.0 g, 3.2 mmol) ethanol ( 10 mL) solution was added to Raney Ni (1 g). The reaction mixture was stirred under hydrogen atmosphere at 1 atmosphere overnight. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad to remove the catalyst and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane solution of 10% methanol as eluent to afford the target product tert-butyl 3-oxo-2,8-diazaspiro[4,5]decane-8-carboxylate (694 mg, 86% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CD3OD): δ 3.54-3.48 (m, 2H), 3.37-3.32 (m, 2H), 3.23 (s, 2H), 2.26 (s, 2H), 1.62-1.59 (m, 4H), 1.45 (s, 9H). | [References]
[1] Patent: US2006/19985, 2006, A1. Location in patent: Page/Page column 55
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 19, p. 3772 - 3779
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 3866 - 3874
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 22, p. 6375 - 6378
[5] Patent: WO2015/140559, 2015, A1. Location in patent: Page/Page column 44 |
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