tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate Chemical Properties

Melting point:

55-56℃

Boiling point:

349℃

Density 

1.12

Flash point:

165℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

solid

pka

-0.80±0.20(Predicted)

color 

Clear yellow

InChI

InChI=1S/C13H21NO3/c1-12(2,3)17-11(16)14-6-4-13(5-7-14)8-10(15)9-13/h4-9H2,1-3H3

InChIKey

SIMIIXFMGJYGLR-UHFFFAOYSA-N

SMILES

C1C2(CCN(C(OC(C)(C)C)=O)CC2)CC1=O

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

29339900

tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate Usage And Synthesis

Uses

2-O-7-azaspiro[3.5]nonane-7-carboxylic acid tert-butyl ester is an organic intermediate commonly used in drug design. It has been reported in the literature to be used in the preparation of compound 2-[2,6-difluoro-4-(4-methanesulfonylphenyl)phenoxy]-7-azaspirocyclic[3.5]nonane-7-carboxylic acid tert-butyl ester, a GPR119 agonist used to treat diseases such as diabetes and metabolic disorders.

Chemical Properties

White powder

Synthesis

To a flame-dried RB flask with tert-butyl 4-methylenepiperidine-1- carboxylate (2.96 g, 15 mmol, 1.0 equiv) and Zn/Cu couple (6.54 g, 172.5 mmol, 11.5 equiv) under vacuum, t-BuOMe (60 mL) was charged and refilled the flask with N2 balloon. To the mixture thus obtained stirred at 15 °C, a solution of 2,2,2- trichloroacetyl chloride in DME (20 mL) was added dropwise. The mixture was stirred at room temperature overnight after addition. To the reaction mixture stirred in an external ice- bath, a saturated solution of NH4CI (60 mL) was added slowly and carefully (especially the first few drops). After addition, the mixture was stirred at room temperature for 4 h and filtered to remove the solid. The phases were separated. The aqueous phase was extracted with EtOAc. The combined organic phase was washed with brine, dried over anhydrous Na2S04, and concentrated to give the residue, which was purified by CombiFlash (40 g silica gel column, EtOAc/Hexane: 0-40percent) to afford 619 mg (15%) of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate.

References

[1] Patent: CN106674112, 2017, A. Location in patent: Paragraph 0037-0038
[2] Patent: WO2013/13308, 2013, A1. Location in patent: Paragraph 00199-00201

tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate(203661-69-2)Related Product Information

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