Bicyclo[2.2.2]octane-1,4-dicarboxylic acid hemimethyl ester

Product NameBicyclo[2.2.2]octane-1,4-dicarboxylic acid hemimethyl ester
CAS18720-35-9
MFC11H16O4
MW212.24
EINECS814-024-1
MOL File18720-35-9.mol

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
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Eye Irrit. 2

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

dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate

1459-96-7

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

18720-35-9

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

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

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