TERT-BUTYL 3-OXO-2,8-DIAZASPIRO[4.5]DECANE-8-CARBOXYLATE Chemical Properties

Boiling point:

425℃

Density 

1.15

Flash point:

211℃

storage temp. 

2-8°C

pka

16.26±0.20(Predicted)

Appearance

White to light yellow Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2933998090

TERT-BUTYL 3-OXO-2,8-DIAZASPIRO[4.5]DECANE-8-CARBOXYLATE Usage And Synthesis

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

TERT-BUTYL 3-OXO-2,8-DIAZASPIRO[4.5]DECANE-8-CARBOXYLATE(169206-67-1)Related Product Information

• 7-Methoxy-1H,2H,3H,4H,5H-benzo[d]azepine HCl
• 5-Trifluoromethyl-2H-pyridazine-2-one
• 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, methyl ester
• 1H-Indole-7-carbonitrile,4-fluoro-(9CI)
• (2-Pyridinyloxy)acetic acid
• Pyrido[4,3-d]pyrimidin-5(6H)-one, 2,4-dichloro-7,8-dihydro-
• No Chinese name
• 5-chloro-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one
• 3-iodo-2-Methyl-1H-pyrrolo[2,3-b]pyridine
• TERT-BUTYL 3-OXO-2,8-DIAZASPIRO[4.5]DECANE-8-CARBOXYLATE
• 2,8-DIAZA-SPIRO[4.5]DECANE-8-CARBOXYLIC ACID TERT-BUTYL ESTER
• 8-METHYL-2,8-DIAZASPIRO[4.5]DECAN-3-ONE