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

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

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

• 74530-56-6 tert-butyl 4-chloroacetoacetate 
• 125971-93-9 (3R,5R)-tert-butyl-6-cyano-3,5-dihydroxyhexanoate 
• 154026-94-5 (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester 
• 74530-57-7 tert-butyl 4-bromoacetoacetate 
• 109462-44-4 (R)-3-hydroxy-5-hexenoic acid methyl ester 
• 181272-46-8 (2R)-1-cyano-2-hydroxy-4-pentene 
• 950513-91-4 (R)-tert-butyl 5-hydroxy-3-oxoocto-7-enoate 

Downstream Products

• 265989-39-7 (4R-cis)-1,1-dimethylethyl-6-[2-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(4-benzyloxyphenyl)carbonyl]-1H-pyrrol-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate 
• 163217-68-3 tert-butyl 2-((4R,6R)-6-(2-(3-((4-(benzyloxy)phenyl)carbamoyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 
• 265989-34-2 C₄₀H₄₂⁽²⁾H₅FN₂O₅ 
• 265989-41-1 C₄₇H₄₈⁽²⁾H₅FN₂O₆ 
• 265989-37-5 C₄₇H₄₈⁽²⁾H₅FN₂O₆ 
• 845280-54-8 [2-((4R,6R)-6-tert-Butoxycarbonylmethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethylamino]-(4-fluoro-phenyl)-acetic acid methyl ester 
• 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 
• 134523-00-5 atorvastatin 
• 867308-77-8 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 ester 
• 1319747-74-4 C₃₄H₄₃FN₂O₆ 
• 1319747-73-3 C₃₃H₄₁FN₂O₆ 
• 1319747-72-2 C₃₂H₃₉FN₂O₆ 
• 1303969-83-6 C₃₁H₄₁N₅O₅ 
• 1303969-87-0 C₃₁H₄₃N₅O₄ 

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.

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.

A atorvastatin sandbank calcium chiral synthesis of intermediates method

The invention discloses a synthesis method for a chiral intermediate of atorvastatin calcium, and belongs to the technical field of medical intermediate synthesis. The synthesis method is characterized in that according to the process route, not only are dangerous, highly toxic and expensive chemicals such as butyl lithium, editpotassium cyanide and periodic acid in chemical synthesis prevented from being used, but also an ee value of the chiral intermediate is effectively improved due to usage of a mixed chiral catalysts of titanium iso-propylate and S-xenol. According to the synthesis method, the raw materials are low in cost and easy to obtain, the route operation is easy, the repeatability is good, the yield is very high, and the synthesis method is 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.

Preparation method of synthetic intermediate of Lipitor

The invention discloses a novel preparation method for a side-chain fragment compound, ATS-9, of Lipitor and solves a problem that poisonous reagents, such as Raney nickel, are required in synthesis in the prior art. The preparation method includes the steps of: with epoxy chloropropane as an initial raw material, performing a ring opening reaction with Grignard reagent to obtain a first chiral hydroxyl group; performing cyano substitution, hydrolyzing the substituted cyano group into ester, performing homologation reaction to extend the carbon chain, and performing reduction with diethylmethoxylborane and sodium borohydride, and protecting the two hydroxyl groups and finally performing the Staudinger reaction to prepare the ATS-9.

Photochemical Formation and Cleavage of C-N Bond

A new photochemical method of C-N bond formation has been developed. A properly substituted trityl alcohol can cleave the benzylic C-O bond and replace it with a C-N bond which is stable under the irradiation conditions. The C-N bond can then be photochemically cleaved with the same light source when the nitrogen is protonated. (Chemical Presented).

An improved process for chiron synthesis of the atorvastatin side chain

An improved and practical synthesis of tert-butyl ((4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetate 3 has been developed for supplying this key chiral side-chain of atorvastatin by using a Blaise reaction of (S)-4-chloro-3-((trimethylsilyl)oxy)butanenitrile 7 and the Raney Ni catalyzed hydrogenation of tert-butyl 2-((4R,6R)-6-(-2-oximeethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 12 as the key steps. This nine-step route from (R)-epichlorohydrin afforded the target compound in 55% overall yield of high chemical and enantiomeric purity.

THIOAMIDE COMPOUND, METHOD FOR PRODUCING THIOAMIDE COMPOUND, METHOD FOR PRODUCING [(4R,6R)-6-AMINOETHYL-1,3-DIOXANE-4-YL]ACETATE DERIVATIVE, AND METHOD FOR PRODUCING ATORVASTATIN

A thioamide compound represented by the following general formula (1): wherein, in the general formula (1), R1 represents one of -OR11 and -NR12R13; R2 and R3 each independently represent one of a protecting group of an amide group and a hydrogen atom; the R11 represents one of a protecting group of a hydroxyl group and a hydrogen atom; and the R12 and R13 each independently represent one of a protecting group of an amino group and a hydrogen atom, where the R12 and R13 may together form a protecting group having a cyclic structure.

Microencapsulated catalyst

The present invention relates to a catalyst system. In particular the invention relates to a catalyst in the form of metal or an alloy that is encapsulated within a polymer shell or matrix. More specifically the invention is directed towards reactive catalytic metals that may be pyrophoric or otherwise reactive in air and/or susceptible to oxidation. In particular, the invention is concerned with catalysts based on nickel.