125995-13-3

Basic information

• Product Name: (4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate
• Synonyms: (4R,CIS)-1,1-DIMETHYLETHYL-6-AMINOETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;(4R-Cis)-1,1-Dimethylethyl-6-aminoethyl-2,2-dimethyl-1,3-dioxoane-4-acetate;(4R,6R)-T-BUTYL-6-(2-AMINOETHYL)-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;(4R,6R)-TERT-BUTYL-6-(2-AMINOETHYL)-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;ATS-9;TERT-BUTYL[(4R,6R)-6-(2-AMINOETHYL)-2,2-DIMETHYL-1, 3-DIOXAN-4-YL]ACETATE;(4R-CIS)-1,1-DIMETHYLETHYL-6-AMINOETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE (ATS-9);Atorvastatin Intermediate Ⅰ
• CAS NO: 125995-13-3
• Molecular Formula: C₁₄H₂₇NO₄
• Molecular Weight: 273.37
• EINECS: 1308068-626-2
• Product Categories: INTERMEDIATESOFATORVASTATIN;chiral;ATORVASTATIN CALCIUM;(intermediate of atorvastatin);Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Chiral Reagents
• Mol File: 125995-13-3.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 339.8 °C at 760 mmHg
• Flash Point: 96.8 °C
• Appearance: Light yellow to green or light blue/Viscous Liquid
• Density: 0.992 g/cm³
• Vapor Pressure: 8.94E-05mmHg at 25°C
• Refractive Index: 1.454-1.456
• Storage Temp.: Refrigerator
• Solubility: soluble in Chloroform
• PKA: 9.80±0.10(Predicted)
• CAS DataBase Reference: (4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate(125995-13-3)
• EPA Substance Registry System: (4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate(125995-13-3)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 125995-13-3(Hazardous Substances Data)

Usage

Description

(4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers at the 4R and 6R positions, a tert-butyl group, an aminoethyl substituent, and a dimethyl-1,3-dioxane core with an acetate group at the 4-position. This colorless to light yellow liquid exhibits specific chemical properties that make it a valuable synthetic intermediate in various chemical processes.

Uses

Used in Pharmaceutical Industry:
(4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate is used as a synthetic intermediate for the development of pharmaceutical compounds. Its unique structure and functional groups allow for the creation of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
(4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate is used as a key building block in the synthesis of various organic compounds. Its versatile structure enables the formation of a wide range of products, making it a valuable asset in the field of organic chemistry.
Used in Atorvastatin Production:
(4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate is an impurity of Atorvastatin (A791750), a widely used drug for the treatment of high cholesterol and related cardiovascular conditions. Its presence in the production process highlights the importance of controlling impurities to ensure the safety and efficacy of the final product.

InChI:InChI=1/C14H27NO4/c1-13(2,3)19-12(16)9-11-8-10(6-7-15)17-14(4,5)18-11/h10-11H,6-9,15H2,1-5H3/p+1/t10-,11-/m1/s1

Upstream product

• 1331869-22-7 tert-butyl 2-((4R,6R)-2,2-dimethyl-6-(2-(tosyloxy)ethyl)-1,3-dioxan-4-yl)acetate 
• 1173184-84-3 tert-butyl 2-[(4R,6R)-6-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 1331869-21-6 tert-butyl 2-((4R,6R)-6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 
• 1331869-20-5 (R)-tert-butyl 7-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-3-oxoheptanoate 
• 1347738-07-1 (R)-N,N-diallyl-5-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)pentanethioamide 
• 1331869-16-9 (R)-N,N-diallyl-5-(benzyloxy)-3-hydroxypentanethioamide 
• 619261-20-0 tert-butyl [(4R,6S)-6-(1-acetoxy-2-nitroethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 619261-19-7 tert-butyl [(4R,6S)-6-(1-hydroxy-2-nitroethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 124752-23-4 tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 124655-09-0 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate 
• 682356-86-1 [(4R,6R)-6-(2-Azido-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester 
• 682356-87-2 [(4R,6R)-6-(2-Azido-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid 
• 682356-88-3 tert-butyl 2-((4R,6R)-6-(2-azidoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 
• 619261-21-1 tert-butyl [(4R,6R)-2,2-dimethyl-6-(2-nitroethyl)-1,3-dioxan-4-yl]acetate 

Downstream Products

• 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 
• 1303969-87-0 C₃₁H₄₃N₅O₄ 
• 1303969-83-6 C₃₁H₄₁N₅O₅ 
• 134523-00-5 atorvastatin 
• 676260-70-1 (4S,6S)-6-(2-aminoethyl)-4-hydroxytetrahydro-2H-pyran-2-one 
• 501121-34-2 (-)-Atorvastatin 
• 581772-29-4 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid 
• 867304-09-4 1-[2-((4R,6R)-6-tert-Butoxycarbonylmethyl-2,2-dimethyl[1,3]dioxan-4-yl)-ethyl]-2-(4-fluoro-phenyl)-5-isopropyl-1H-imidazole-4-carboxylic acid 
• 1071147-05-1 C₃₁H₄₀FN₃O₅ 
• 867308-86-9 1-[2-((4R,6R)-6-tert-butoxycarbonylmethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-2-(4-fluoro-phenyl)-5-isopropyl-1H-imidazole-4-carboxylic acid benzyl amide 
• 134523-03-8 lipitor 

Relevant articles and documents

AN IMPROVED AND COMMERCIALLY VIABLE PROCESS FOR PREPARATION OF PYRROLE DERIVATIVES WITH IMPROVED IMPURITY PROFILE & MINIMISATION OF UNIT OPERATIONS.

The present invention relates to improved process for the preparation of a pyrrole derivative as a racemic mixture, an enantiomer, a diastereoisomer, a mixture thereof, a tautomer thereof or a pharmaceutically acceptable salt and hydrates thereof and also intermediates involved therein. Particularly invention is directed to improved processes for the preparation of pyrrole derivatives such as (4R,cis)-6-[2-[3-phenyl-4-(phenyl-carbamoyl)-2-(4-fluorophenyl)-5-(1-methyl-ethyl)-pyrrole-1-yl]-2,2-dimethyl-[1,3]dioxane-4-yl-acetic acid-tertiary butyl ester of formula IV followed by its conversion into [R-(R*, R*]-2-(4-fluorophenyl)- β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1- heptanoic acid particularly calcium salt and its hydrate represented by Formulae I/IA respectively wherein formation of the impurities is either eliminated or minimized in the corresponding intermediaries.

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.

2 - ((4R, 6R) - 6-aminomethyl-ethyl -2,2-dimethyl -1,3-dioxane-4-yl) acetate simple method for preparing

The invention relates to a simple preparation method of 2-((4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxyhexacyclo-4-yl)acetate (I). The method comprises the following steps: reacting 3-cyanopropylene (II) and 3,3-dialkoxypropionate (III) or 3-alkoxyacrylate (IV) under the catalytic action of Lewis acid to prepare 2-((4R,6R)-6-cyanomethyl-2-ester-methyl-1,3-dioxyhexacyclo-4-yl)acetate (V), removing the solvent, directly carrying out blocking group conversion to prepare 2-((4R,6R)-6-cyanomethyl-2,2-dimethyl-1,3-dioxyhexacyclo-4-yl)acetate (VI), and carrying out Raney nickel catalytic hydrogenation two-step reaction to prepare (I). The stable form of the hexatomic ring chair-structure equatorial bond is utilized to construct the chiral center without using any additional chiral assistant. The method has the advantages of accessible raw materials, short reaction procedure and low cost, avoids carbonyl asymmetric reduction, is simple and environment-friendly, and is industrial production.