1428243-26-8

Basic information

• Product Name: (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
• Synonyms: (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester;intermediate of abt594;(3R,4S)-benzyl 3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate
• CAS NO: 1428243-26-8
• Molecular Formula: C₁₆H₂₀BrNO₃
• Molecular Weight: 354.2389
• EINECS: -0
• Mol File: 1428243-26-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 453.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.361±0.06 g/cm3(Predicted)
• PKA: -2.91±0.60(Predicted)
• CAS DataBase Reference: (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester(1428243-26-8)
• EPA Substance Registry System: (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester(1428243-26-8)

Safety Data

• Hazardous Substances Data: 1428243-26-8(Hazardous Substances Data)

Usage

Description

(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester is a complex organic compound with a specific stereochemistry and functional groups. It is characterized by its molecular structure, which includes a bromoacetyl group, an ethyl group, and a phenylmethyl ester group attached to a pyrrolidinecarboxylic acid backbone. (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester is synthesized through a series of chemical reactions and is known for its potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester is used as a reagent for the preparation of imidazopyrrolopyrazine derivatives and analogs. These derivatives are of significant interest due to their potential as protein kinase modulators, which play a crucial role in various cellular processes and are often targeted in the development of therapeutic agents for various diseases, including cancer and inflammatory disorders.
Used in Chemical Research:
In addition to its pharmaceutical applications, (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester can also be utilized in chemical research as a starting material or intermediate for the synthesis of other complex organic molecules. Its unique structure and functional groups make it a valuable compound for exploring new chemical reactions and developing novel synthetic pathways.

Upstream product

• 51814-19-8 1-Benzyloxycarbonyl-4-ethoxycarbonyl-3-oxopyrrolidine 
• 17085-88-0 diethyl propylidenemalonate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 23114-01-4 N-methyl-N-nitroso-p-toluenesulfonamide 

Downstream Products

• 1428243-27-9 (3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate 
• 1310726-60-3 (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide 
• 1428243-28-0 8-((3R,4S)-4-ethylpyrrolidin-3-yl)-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine 

Relevant articles and documents

Development of a Scalable Enantioselective Synthesis of JAK Inhibitor Upadacitinib

Process development of a six-stage synthesis of upadacitinib, a JAK1 inhibitor, is described. It is highlighted by an enantioselective and diastereoselective hydrogenation of a tetrasubstituted olefin to set the two pyrrolidine stereocenters. Preparation of the main fragments and strategies to link them together, optimization of the imidazole cyclization, and in-depth understanding of the formation of the urea moiety at the final stage are discussed.

Preparation method and application of 1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid

The invention relates to a preparation method and application of 1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid. The preparation method comprises the following steps: carrying out hydrogenation reaction on a compound I-1 to obtain a compound II, and carrying out reaction on the compound II to obtain the 1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid. Compared with the prior art, the synthesis method is simple in route, convenient to operate, safe and reliable; the method is environment-friendly; efficiency is high and cost is low; and the synthesis method has good chemical selectivity and enantioselectivity, and the product purity and optical purity are high. The 1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid prepared by the method can be further used for preparing a compound benzyl 3-(2-bromoacetyl)-4-ethylpyrrolidine-1-formate which is an important intermediate for preparing a selective JAK1 inhibitor; and therefore, the synthetic route provided by the invention also has important significance on the production of the selective JAK1 inhibitor.

THE PROCESS FOR THE PREPARATION OF UPADACITINIB AND ITS INTERMEDIATES

The present invention provides an improved process for the preparation Upadacitinib by using novel intermediates. The present invention also provides processes for the preparation of novel intermediates of Upadacitinib.