7-Oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid, 1,1-dimethylethyl ester Chemical Properties

Boiling point:

272.5±23.0 °C(Predicted)

Density 

1.141±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

pka

-0.83±0.20(Predicted)

color 

Colorless to Light orange to Yellow

InChI

InChI=1S/C10H17NO3/c1-10(2,3)14-9(12)11-5-4-7-8(6-11)13-7/h7-8H,4-6H2,1-3H3

InChIKey

MMPWHAJQEZIIEH-UHFFFAOYSA-N

SMILES

C12C(O1)CCN(C(OC(C)(C)C)=O)C2

Safety Information

HS Code 

2918300090

7-Oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid, 1,1-dimethylethyl ester Usage And Synthesis

Synthesis

The general procedure for the synthesis of tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate from N-Boc-1,2,3,6-tetrahydropyridine was carried out as follows: tert-butyl 5,6-dihydropyridine-1(2H)-carboxylate (2.00 g, 10.9 mmol) was dissolved in dichloromethane (DCM) as described in the literature WO 97/10212 and added with m-chloroperoxybenzoic acid (MCPBA, 4.16 g, 18.6 mmol). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was washed sequentially with saturated aqueous sodium metabisulfite solution, saturated aqueous sodium bicarbonate solution, 1N aqueous sodium hydroxide solution and saturated brine. The organic layer was separated, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (2.04 g, 94% yield) as an oil. The product was characterized by 1H NMR (400 MHz, CDCl3) with chemical shift δ of 1.45 (s, 9H), 1.91 (m, 1H), 2.04 (br, 1H), 3.11 (m, 1H), 3.21 (br, 1H), 3.29 (m, 1H), 3.45 (br, 1H), 3.70 (br, 1H), 3.88 (br 1H).

References

[1] Tetrahedron Letters, 2004, vol. 45, # 37, p. 6841 - 6845
[2] Organic Process Research and Development, 2014, vol. 18, # 2, p. 321 - 330
[3] Patent: WO2008/11130, 2008, A2. Location in patent: Page/Page column 136-137
[4] Patent: WO2013/138210, 2013, A1. Location in patent: Paragraph 0243
[5] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 39 - 52

7-Oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid, 1,1-dimethylethyl ester(161157-50-2)Related Product Information

• tert-butyl 7-oxo-2,6-diazaspiro[3.4]octane-2-carboxylate
• Tert-Butyl 7-Oxo-5-Azaspiro[2.4]Heptane-5-Carboxylate
• Tert-Butyl7-oxo-3-azabicyclo[3.3.1]nonane-3-carboxylate
• tert-butyl 8-oxo-3-azabicyclo[3.2.1]octane-3-carboxylate
• tert-Butyl 8-oxa-2-azaspiro[4.5]decane-2-carboxylate
• tert-butyl 7-oxo-4-azaspiro[2.5]octane-4-carboxylate
• tert-Butyl 7-oxo-2-azaspiro[3.5]nonane-2-carboxylate
• tert-Butyl 7-oxo-5-oxa-2-azaspiro[3.4]octane-2-carboxylate