125971-94-0

Basic information

• Product Name: (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate
• Synonyms: ATS-8;(4R,6R)-T-BUTYL-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;(4R,6R)-TERT-BUTYL-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;(4R,CIS)-1,1-DIMETHYLETHYL-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;(4R,3R)-TERT-BUTYL-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;tert-Butyl (4R,3R)-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate;TERT-BUTYL[(4R,6R)-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXAN-4-YL]ACETATE;(4R-CIS)-1,1-DIMETHYLETHYL-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE (ATS-8)
• CAS NO: 125971-94-0
• Molecular Formula: C₁₄H₂₃NO₄
• Molecular Weight: 269.34
• EINECS: 425-780-3
• Product Categories: Chemical intermediate for Atorvastatin Calcium;INTERMEDIATESOFATORVASTATIN;chiral;(intermediate of atorvastatin);Chiral Building Blocks;Cyanides/Nitriles;Organic Building Blocks;Atorvastatin intermediates
• Mol File: 125971-94-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 65-69 °C(lit.)
• Boiling Point: 364.1 °C at 760 mmHg
• Flash Point: 159.2 °C
• Appearance: white to light yellow crystal powder
• Density: 1.016 g/cm³
• Vapor Pressure: 1.73E-05mmHg at 25°C
• Refractive Index: 1.439
• Storage Temp.: 2-8°C
• Solubility: soluble in Chloroform
• CAS DataBase Reference: (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate(125971-94-0)
• EPA Substance Registry System: (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate(125971-94-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 125971-94-0(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 125971-94-0 differently. You can refer to the following data:
1. Atorvastatin Intermediate
2. (4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl Ester is an intermediate of Atorvastatin (A791750, Ca salt), 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.

InChI:InChI=1/C14H23NO4/c1-13(2,3)19-12(16)9-11-8-10(6-7-15)17-14(4,5)18-11/h10-11H,6,8-9H2,1-5H3/t10-,11-/m1/s1

Upstream product

• 143-33-9 sodium cyanide 
• 141942-87-2 [(4R,6S)-6-(4-Chloro-benzenesulfonyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester 
• 141942-88-3 [(4R,6S)-6-(4-Bromo-benzenesulfonyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester 
• 141942-89-4 tert-butyl 2-[(4R,6S)-2,2-dimethyl-6-[(4-nitrophenylsulfonyloxy)methyl]-1,3-dioxan-4-yl]acetate 
• 791115-48-5 ((4R,6R)-6-cyanomethyl-2,2-dimethyl-[1,3]-dioxan-4-yl)-acetic acid chloride 
• 75-65-0 tert-butyl alcohol 
• 74530-57-7 tert-butyl 4-bromoacetoacetate 
• 74530-56-6 tert-butyl 4-chloroacetoacetate 
• 154026-94-5 (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester 
• 848644-99-5 (5R)-1,1-dimethylethyl 6-cyano-5-hydroxy-3-oxo-hexanoate 
• 7397-46-8 diethyl methoxy borane 
• 125971-93-9 (3R,5R)-tert-butyl-6-cyano-3,5-dihydroxyhexanoate 
• 773837-37-9 sodium cyanide 
• 125971-92-8 (R)-1,1-dimethylethyl 6-cyano-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3oxohexanoate 

Downstream Products

• 134523-03-8 lipitor 
• 125971-95-1 tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate 
• 134395-00-9 (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester 
• 134523-01-6 atorvastatin sodium 
• 125971-86-0 tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate 

Relevant articles and documents

Atorvastatin calcium intermediate as well as preparation method and application thereof

The invention discloses an atorvastatin calcium intermediate as well as a preparation method and application thereof. A synthesis process of the intermediate is environmentally-friendly, simple to operate and low in EHS risk; raw materials are easy to obtain; a used chemical reagent is small in toxicity and low in cost; and the synthesis process is a green synthesis process suitable for the industrial production. Moreover, the intermediate provided by the invention is applied to the synthesis of atorvastatin calcium and a key intermediate thereof, the route is relatively short, the yield is high, the industrial production cost of the atorvastatin calcium is effectively reduced, and the atorvastatin calcium intermediate has a relatively high industrial application prospect.

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.

Atorvastatin calcium side chain intermediate preparation method

The present invention provides an atorvastatin calcium side chain intermediate preparation method comprising the following steps: (1) a compound II is added into 2,2-dimethoxypropane liquid, the molar ratio of compound II to 2,2-dimethoxypropane is 1: 2.2 to 13.2; (2) an acidic resin catalyst with the mass accounting for 2.6 to 9.5% of the mass of the compound II is added, and at 10-30DEG C, the mixture is stirred for reaction for 4-6 hours; and (3) the reaction system is filtered, filtrate is concentrated to obtain an oil matter, and the oil matter is recrystallized to obtain a solid atorvastatin calcium side chain intermediate I. By the method, the solid atorvastatin calcium side chain intermediate I with the purity of more than 99% is obtained, and the yield is greater than 95%. The reaction conditions are mild, decolorization treatment is not required, production cost is low, the reaction is stable and easy to control, safety is high, operation is easy, the catalyst and the reactant 2,2-dimethoxypropane are recyclable, waste liquids and waste residues are not produced, and the method is green and environmentally-friendly.