196085-84-4

Basic information

• Product Name: (4R,6S)-tert-Butyl-6-cyanoMethyl-2,2-diMethyl-1,3-dioxane-4-acetate
• Synonyms: (4R,6S)-tert-Butyl-6-cyanoMethyl-2,2-diMethyl-1,3-dioxane-4-acetate;tert-Butyl 2-((4R,6S)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;Atorvastatin Impurity 19
• CAS NO: 196085-84-4
• Molecular Formula: C14H23NO4
• Molecular Weight: 269.33672
• Mol File: 196085-84-4.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 364.1±17.0 °C(Predicted)
• Appearance: /
• Density: 1.016±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (4R,6S)-tert-Butyl-6-cyanoMethyl-2,2-diMethyl-1,3-dioxane-4-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,6S)-tert-Butyl-6-cyanoMethyl-2,2-diMethyl-1,3-dioxane-4-acetate(196085-84-4)
• EPA Substance Registry System: (4R,6S)-tert-Butyl-6-cyanoMethyl-2,2-diMethyl-1,3-dioxane-4-acetate(196085-84-4)

Safety Data

• Hazardous Substances Data: 196085-84-4(Hazardous Substances Data)

Usage

Uses

(4R,6S)-6-(Cyanomethyl)-2,2-dimethyl--1,3-dioxane-4-acetic Acid tert-Butyl Ester is an impurity in the synthesis of Atorvastatin (A791750), a selective, competitive HMG-CoA reductase . Atorvastatin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglyceinhibitorrides in patients with hypercholesterolemia.

Upstream product

• 125971-93-9 (3R,5R)-tert-butyl-6-cyano-3,5-dihydroxyhexanoate 
• 807312-27-2 (6-cyanomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid 
• 75-65-0 tert-butyl alcohol 
• 144-55-8 sodium hydrogencarbonate 
• 77-76-9 2,2-dimethoxy-propane 
• 312745-90-7 tert-butyl (5S)-6-cyano-5-hydroxy-3-oxohexanoate 
• 143-33-9 sodium cyanide 
• 141942-89-4 tert-butyl 2-[(4R,6S)-2,2-dimethyl-6-[(4-nitrophenylsulfonyloxy)methyl]-1,3-dioxan-4-yl]acetate 
• 141942-88-3 [(4R,6S)-6-(4-Bromo-benzenesulfonyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester 
• 141942-87-2 [(4R,6S)-6-(4-Chloro-benzenesulfonyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester 
• 1105067-92-2 tert-butyl (3S,5S)-6-cyano-3,5-dihydroxyhexanoate 
• 773837-37-9 sodium cyanide 

Relevant articles and documents

An improved synthesis of 1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, a key intermediate for atorvastatin synthesis

An improved synthesis of 1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, a key intermediate for the synthesis of an effective HMG-CoA reductase inhibitor atorvastatin, is described. The synthesis is based on the iodolactonization of hepta-1,6-dien-4-ol to 4-allyl-6-iodomethyl-1,3-dioxan-2-one, which was converted in several steps to (6-allyl-2,2-dimethyl-1,3-dioxan-4-yl)-acetonitrile. This intermediate provided (6-cyanomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid either via the corresponding aldehyde or via (2,2-dimethyl-6-oxiranylmethyl-1,3-dioxan-4-yl)acetonitrile.

Preparation method of atorvastatin calcium intermediate

The invention belongs to the field of medicines and chemical industry, and particularly relates to the field of pharmacy, in particular to a preparation method of an atorvastatin calcium intermediate.The preparation method comprises the following steps: firstly preparing a compound II into a lithium reagent, then reacting with methyl chloroformate, introducing an ester group, aminolyzing the ester group into amine, dehydrating the amide, and finally reducing a cyano group to obtain a target compound. By the brand-new preparation method of the atorvastatin calcium intermediate, a compound VI can be synthesized under the premise that highly toxic substances such as hydrocyanic acid, hydrobromide and the like are not used, and the compound VI is used for preparing a compound I; reagents usedin the whole preparation process are safe and environment-friendly, and the preparation method is more suitable for industrial production.

A atorvastatin condensation the intermediate product of the resolution method (by machine translation)

The invention relates to a kind of atorvastatin "condensate" intermediate resolution method, the method, comprises the following steps: step 1, takes shrinks compound trans-isomer mixture, in order to isopropanol as the solvent heating and dissolves it, s