101692-01-7

Basic information

• Product Name: Treprostinil intermediate
• Synonyms: Treprostinil intermediate;(alphaS,1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-2-hydroxy-5-methoxy-alpha-pentyl-1H-benz[f]indene-1-propanol;(1R,2R,3aS,9aS)-1-(2-Hydroxyoctyl)-5-methoxy-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-2-ol;(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-5-methoxy-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-2-ol;(1R,2R,3aS,9aS)-1-((S,E)-3-hydroxyoct-1-en-1-yl)-5-methoxy-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-2-ol;Descarboxy Treprostinil
• CAS NO: 101692-01-7
• Molecular Formula: C₂₂H₃₄O₃
• Molecular Weight: 346.50356
• Mol File: 101692-01-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 71-72 °C
• Boiling Point: 509.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.062±0.06 g/cm3(Predicted)
• PKA: 15.10±0.40(Predicted)
• CAS DataBase Reference: Treprostinil intermediate(CAS DataBase Reference)
• NIST Chemistry Reference: Treprostinil intermediate(101692-01-7)
• EPA Substance Registry System: Treprostinil intermediate(101692-01-7)

Safety Data

• Hazardous Substances Data: 101692-01-7(Hazardous Substances Data)

Usage

Description

Treprostinil intermediate is a synthetic analog of Prostacyclin, which is a naturally occurring hormone with vasodilatory and antihypertensive properties. It is an essential compound in the synthesis of Treprostinil (T719500), an active pharmaceutical ingredient used in the treatment of pulmonary arterial hypertension (PAH). The intermediate plays a crucial role in the development of medications that help manage and alleviate the symptoms of PAH.

Uses

Used in Pharmaceutical Industry:
Treprostinil intermediate is used as an active pharmaceutical ingredient for the development of medications that treat pulmonary arterial hypertension (PAH). It serves as a synthetic analog of Prostacyclin, which is known for its vasodilatory and antihypertensive effects, making it a valuable compound in the creation of effective treatments for PAH.
Additionally, Treprostinil intermediate is used as an impurity in the synthesis of Treprostinil (T719500), which is marketed under the trade name Remodulin. This medication is specifically designed to manage the symptoms of PAH, providing patients with a viable treatment option to improve their quality of life and overall health.

Upstream product

• 94956-98-6 2-allyl-3-methoxybenzaldehyde 

Downstream Products

• 830354-48-8 2-(((1R,2R,3aS,9aS)-2-hydroxy-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yl)oxy)acetic acid diethanolamine salt 
• 1355990-07-6 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester 
• 81846-19-7 treprostinil 
• 101692-02-8 (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol 

Relevant articles and documents

The Intramolecular Asymmetric Pauson-Khand Cyclization As A Novel and General Stereoselective Route to Benzindene Prostacyclins: Synthesis of UT-15 (Treprostinil)

A general and novel solution to the synthesis of biologically important stable analogues of prostacyclin PGI2, namely benzindene prostacyclins, has been achieved via the stereoselective intramolecular Pauson-Khand cyclization (PKC). This work illustrates for the first time the synthetic utility and reliability of the asymmetric PKC route for synthesis and subsequent manufacture of a complex drug substance on a multikilogram scale. The synthetic route surmounts issues of individual step stereoselectivity and scalability. The key step in the synthesis involves efficient stereoselection effected in the PKC of a benzoenyne under the agency of the benzylic OTBDMS group, which serves as a temporary stereodirecting group that is conveniently removed via benzylic hydrogenolysis concomitantly with the catalytic hydrogenation of the enone PKC product. Thus the benzylic chiral center dictates the subsequent stereochemistry of the stereogenic centers at three carbon atoms (C3a, C9a, and C1).