491833-29-5

Basic information

• Product Name: Eliglustat
• Synonyms: Eliglustat;Genz 99067;N-[(1R,2R)-2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-hydroxy-1-(1-pyrrolidinylmethyl)ethyl]-octanamide;N-[(1R,2R)-1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(1- pyrrolidinyl)-2-propanyl]octanamide;Eliglustat(Genz-99067)
• CAS NO: 491833-29-5
• Molecular Formula: C₂₃H₃₆N₂O₄
• Molecular Weight: 404.54294
• Mol File: 491833-29-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 615.5±55.0 °C(Predicted)
• Appearance: /
• Density: 1.123±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.45±0.20(Predicted)
• CAS DataBase Reference: Eliglustat(CAS DataBase Reference)
• NIST Chemistry Reference: Eliglustat(491833-29-5)
• EPA Substance Registry System: Eliglustat(491833-29-5)

Safety Data

• Hazardous Substances Data: 491833-29-5(Hazardous Substances Data)

Usage

Uses

Eliglustat is a specific and potent inhibitor of glucosylceramide synthase.

Definition

ChEBI: A carboxamide obtained by formal condensation of the carboxy group of octanoic acid with the primary amino group of (1R,2R)-2-amino-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(pyrrolidin-1-yl)propan-1-ol. A ceramide glucosyltr nsferase inhibitor used (as its tartrate salt) for treatment of Gaucher's disease.

Upstream product

• 2879-20-1 1,4-benzodioxan-6-yl methyl ketone 
• 35970-31-1 2-amino-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-one hydrochloride 
• 4629-54-3 2-bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanone 
• 1282295-32-2 C₁₂H₁₀N₂O₃ 
• 6761-70-2 2,3-dihydro-1,4-benzodioxine-6-carbonyl chloride 
• 74053-94-4 ethyl 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-oxopropanoate 
• 4442-54-0 2,3-dihydro-1,4-benzodioxin-6-carboxylic acid 
• 14939-91-4 (E)-3,4-ethylenedioxycinnamic acid 

Relevant articles and documents

Eliglustat intermediate and preparation method thereof

The invention relates to an eliglustat intermediate and a preparation method thereof, and provides a series of intermediate compounds for preparing eliglustat, and a preparation method of the intermediates. With the method provided by the invention, raw materials and a transition metal catalyst are subjected to an asymmetric hydrogenation reaction on under certain conditions, and then a series ofreactions are performed to prepare eliglustat. The method provided by the invention is simple and controllable in reaction conditions and easy for industrial production.

A novel method for preparing Eligulstat through chiral resolution

Eliglustat is a ceramide glucosyltransferase inhibitor work as first line oral therapy for adults with Gaucher disease type 1 (a rare disease) at present. Although the eliglustat in enantiomerically pure forms is obtained by asymmetric syntheses, the reported methods suffer from many limits when it comes to industrial applications. Therefore, the preparation of a racemic mixture followed by resolution can still be a viable and straightforward alternative, especially when it could be adapted to large scale. Herein, we developed an effective and practical synthetic route to prepare stereoisomers mixture of eliglustat, and a novel chiral resolution method to prepare eliglustat. Using 1,1′-Binaphthyl-2,2′-diyl -hydrogenphosphate (BNDHP) as resolution reagent, optical pure eliglustat (e.e. >99%, 13.97% total yield) could be obtained after recrystallization.

Development of an Efficient and Scalable Asymmetric Synthesis of Eliglustat via Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation

An efficient and scalable synthesis of eliglustat (1) is herein reported. This novel route features a three-step telescoped process to afford the α-dibenzylamino β-ketoester 6 in 85% overall yield from commercially available 1,4-benzodioxane-6-carboxylic acid 7. The key intermediate 5 was obtained via an efficient ruthenium-catalyzed DKR-ATH reaction, which afforded the desired product in 90% isolated yield with >99:1 dr and 99.7% ee on a 100 g scale. In addition, the amidation of sterically hindered carboxylic acid 14 was optimized and amenable to scale-up. This process not only gives a desirable total yield but also avoids hazardous conditions and chromatographic purification. The robustness of this synthesis was successfully performed on a multigram scale to afford 1 with >99.9% de and >99.9% ee in 56.8% overall yield in nine steps.