BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER Chemical Properties

Melting point:

186.0 to 190.0 °C

Boiling point:

322.5±42.0 °C(Predicted)

Density 

1.307±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystaline

pka

4.77±0.10(Predicted)

color 

White to Almost white

InChI

InChI=1S/C11H16O4/c1-15-9(14)11-5-2-10(3-6-11,4-7-11)8(12)13/h2-7H2,1H3,(H,12,13)

InChIKey

KBZVAQVEHVGIEI-UHFFFAOYSA-N

SMILES

C12(C(OC)=O)CCC(C(O)=O)(CC1)CC2

Safety Information

Hazard Codes 

T

Risk Statements 

25-36

Safety Statements 

26-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HS Code 

2917200090

BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER Usage And Synthesis

Uses

4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic Acid has been used as a reactant for the preparation of bicyclo-octyltriazole inhibitors of HSD1 for metabolic syndrome treatment.

Synthesis

General procedure for the synthesis of 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1,4-dicarboxylic acid from dimethyl bicyclo[2.2.2]octane-1-carboxylate: a mixture of 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid (20 g) and potassium hydroxide (5.5 g) in methanol/water (10:1, 106 mL) was heated to reflux overnight. After the reaction was completed, it was cooled to room temperature and concentrated. The residue was diluted with ethyl acetate and extracted with 1N aqueous sodium hydroxide (2 x 100mL). The organic phase was dried with magnesium sulfate, filtered and concentrated to give the starting material as a white solid. The combined aqueous phases were adjusted to pH 1-2 with 2N aqueous hydrochloric acid and extracted with ethyl acetate (4 x 250mL). The combined turbid organic phases were filtered through a slot filter, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated to afford 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid as a colorless solid (13.1 g, 70% yield). Mass spectral analysis showed [MH]+ = 213.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 24, p. 5731 - 5737
[2] Patent: WO2006/128184, 2006, A2. Location in patent: Page/Page column 164-165
[3] Patent: WO2008/63671, 2008, A2. Location in patent: Page/Page column 177-178
[4] Patent: WO2014/159802, 2014, A1. Location in patent: Paragraph 00189
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 6, p. 1558 - 1568

BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER(18720-35-9)Related Product Information

• 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester,
• Bicyclo[2.2.2]Octane-1,4-Dicarboxylic Acid
• DiMethyl bicyclo[2.2.1]heptane-1,4-carboxylate
• TERT-BUTYL 1-OXO-2,7-DIAZASPIRO[4.5]DECANE-7-CARBOXYLATE
• Tert-butyl 1,7-diazaspiro[4,4]nonane-1-carboxylate
• Tert-butyl 2,6-diazaspiro[3.4]octane-2-carboxylate
• benzyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate
• 2S-7-Aza-bicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-tert-butyl ester
• 7-(TERT-BUTOXYCARBONYL)-1-OXA-2,7-DIAZASPIRO[4.4]NON-2-ENE-3-CARBOXYLIC ACID
• DI-2-PYRIDYL THIONOCARBONATE
• Dibenzyl chloroMethyl phosphate
• (3aR,6as)-tert-butyl 5-methylenehexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate
• DIETHYL 2,5-DIOXOBICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLATE
• TRANS-1,4-CYCLOHEXANEDICARBOXYLIC ACID MONOMETHYL ESTER
• BICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLIC ACID HEMIMETHYL ESTER
• trans-1,4-Cyclohexanedicarboxybic acid
• 1,4-Cyclohexanedicarboxylic acid
• dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate