D-Cyclohexylglycinol: Properties, Applications, and Synthesis
D-Cyclohexylglycinol, also known as (2R)-2-amino-2-cyclohexylethanol, is a chiral amino alcohol with the molecular formula C8H17NO. It belongs to the class of cyclohexylglycine derivatives and has a cyclohexane ring attached to the alpha-carbon of the glycine moiety. The compound is a white to off-white powder with a melting point range of 76-80 °C and a purity of not less than 98% (by HPLC). It is soluble in water, ethanol, and methanol.
Synthesis of D-Cyclohexylglycinol
The synthesis of D-cyclohexylglycinol involves the reaction of cyclohexylmagnesium bromide with N-Boc glycine tert-butyl ester in the presence of a catalyst such as copper(I) chloride or nickel(II) chloride. The resulting intermediate is then treated with hydrochloric acid to remove the Boc protecting group, followed by reduction with sodium borohydride or lithium aluminum hydride to yield D-cyclohexylglycinol in high yield and enantiomeric purity. Other methods for the synthesis of D-cyclohexylglycinol include the catalytic asymmetric hydrogenation of cyclohexenyl glycine derivatives and the resolution of racemic cyclohexylglycinol with chiral acids or bases.
Properties and Applications
D-cyclohexylglycinol has been widely used as a chiral building block and intermediate in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. It is also used as a resolving agent for the separation of racemic mixtures of carboxylic acids, alcohols, and amines. The compound possesses unique stereochemical features that make it a valuable tool for the preparation of enantiopure compounds with high selectivity and efficiency. Some of the notable applications of D-cyclohexylglycinol are described below:
1. Synthesis of antihypertensive agents: D-cyclohexylglycinol has been employed as a key intermediate in the synthesis of several antihypertensive agents, such as cilazapril, benazepril, and fosinopril. These drugs belong to the class of angiotensin-converting enzyme (ACE) inhibitors and are used to treat hypertension, heart failure, and other cardiovascular diseases.
2. Synthesis of anticancer agents: D-cyclohexylglycinol has been used as a starting material for the synthesis of various anticancer agents, including taxol, camptothecin, and podophyllotoxin. These drugs exhibit potent antitumor activity by inhibiting the growth and proliferation of cancer cells.
3. Resolution of chiral compounds: D-cyclohexylglycinol has been utilized as a resolving agent for the separation of racemic mixtures of carboxylic acids, alcohols, and amines. The process involves the formation of diastereomeric salts between the chiral acid or base and the racemic mixture, followed by the selective crystallization of one of the enantiomers.
4. Synthesis of agrochemicals: D-cyclohexylglycinol has been used as a building block for the synthesis of various agrochemicals, such as herbicides, fungicides, and insecticides. These compounds are essential for the protection of crops and plants from pests and diseases.
Conclusion
D-cyclohexylglycinol is a valuable chiral building block and intermediate that has found numerous applications in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique stereochemical features and high enantiomeric purity make it a preferred choice for the preparation of enantiopure compounds with high selectivity and efficiency. The synthesis of D-cyclohexylglycinol involves the reaction of cyclohexylmagnesium bromide with N-Boc glycine tert-butyl ester, followed by deprotection and reduction. Ningbo Inno Pharmchem Co., Ltd. is a reputable manufacturer and supplier of D-cyclohexylglycinol from China, offering high-quality products and competitive prices.
