tras-4-aminocyclohexanecarboxylic acid ethyl ester, CAS No. 1678-68-8

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1678-68-8

Catalog No. EBD242007

CAS 1678-68-8

Name tras-4-aminocyclohexanecarboxylic acid ethyl ester

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Basic Information

Synonyms: tras-4-aminocyclohexanecarboxylicacidethylester ethyltrans-4-aminocyclohexanecarboxylate trans-4-amino-cyclohexane-carboxylicacid-(1)-ethylester trans-4-Amino-cyclohexan-carbonsaeure-(1)-aethylester trans-4-amino-cyclohexanecarboxylicacidethylester trans-4-aminocyclohexanecarboxylicacidethyl trans-4-Amino-cyclohexan-carbonsaeure-1-ethylester TRANS-4-AMINOCYCLOHEXANECARBOXYLICACIDETHYLESTER (trans-4-Carboethoxycyclohexyl)amine cyclohexanecarboxylicacid,4-amino-,ethylester,trans- (1s,4s)-ethyl4-aminocyclohexanecarboxylate

Molecular Formula: C9H17NO2

Molecular Weight: 171.24

MDL Number: MFCD01333991

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

Trans-4-Aminocyclohexanecarboxylic acid ethyl ester is a white to off-white crystalline powder. It is a cyclohexane derivative featuring both an amino group and an ethyl ester group in a trans configuration on the cyclohexane ring. This specific stereochemistry is often crucial for its biological activity and synthetic utility. This compound serves as a key chiral intermediate in the synthesis of various pharmaceutical agents. Its primary application is in the production of antidiabetic drugs, most notably as a critical building block for Sitagliptin, a dipeptidyl peptidase-4 (DPP-4) inhibitor used in the treatment of type 2 diabetes. The trans-4-aminocyclohexyl moiety is a privileged structural motif in medicinal chemistry, contributing to the desired pharmacokinetic and pharmacodynamic properties of the final drug molecule. Beyond its role as a pharmaceutical intermediate, the molecule is also a valuable synthetic building block in organic chemistry. The presence of both a nucleophilic amino group and an electrophilic ester group makes it a versatile precursor for constructing more complex molecular architectures, particularly those containing functionalized cyclohexyl rings.

Physical Properties

Analytical Data

Appearance: Yellow Solid