Desacetyl 2-O-tert-ButyldiMethylsilyl Prasugrel

Base Information

• Chemical Name: Desacetyl 2-O-tert-ButyldiMethylsilyl Prasugrel
• CAS No.: 952340-38-4
• Molecular Formula: C24H32FNO2SSi
• Molecular Weight: 445.673
• Mol file: 952340-38-4.mol

Synonyms:Desacetyl 2-O-tert-ButyldiMethylsilyl Prasugrel

Chemical Property of Desacetyl 2-O-tert-ButyldiMethylsilyl Prasugrel

Chemical Property:

• Boiling Point: 486.3±45.0 °C(Predicted)
• PKA: 3?+-.0.20(Predicted)
• PSA: 57.78000
• Density: 1.167±0.06 g/cm3(Predicted)
• LogP: 6.28760
• Solubility.: Aceton, Chloroform, Dichloromethane, Dimethyl Formamide, Ethyl Acetate

Purity/Quality:

99% ^*data from raw suppliers

Desacetyl2-O-tert-ButyldimethylsilylPrasugrel ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Prasugrel (P701150) and its metabolites.

Technology Process of Desacetyl 2-O-tert-ButyldiMethylsilyl Prasugrel

There total 17 articles about Desacetyl 2-O-tert-ButyldiMethylsilyl Prasugrel which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (204205-33-4) + 5,6,7,7a-tetrahydrothieno[3,2-c]pyridine-2(4H)-one monohydrochloride (109904-37-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (952340-38-4)

Guidance literature:

5,6,7,7a-tetrahydrothieno[3,2-c]pyridine-2(4H)-one monohydrochloride; With triethylamine; In dichloromethane; at 10 ℃; for 0.25h;

tert-butyldimethylsilyl chloride; In dichloromethane; at 10 ℃;

2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone; With triethylamine; sodium iodide; In dichloromethane; at 10 - 25 ℃; Temperature;

Reference yield:

α-cyclopropylcarbonyl-2-fluorobenzyl chloride (178688-43-2) + 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one p-toluenesulfonate (178688-49-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (952340-38-4)

Guidance literature:

5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one p-toluenesulfonate; tert-butyldimethylsilyl chloride; With triethylamine; In dichloromethane; at 25 ℃; for 1h;

α-cyclopropylcarbonyl-2-fluorobenzyl chloride; With triethylamine; sodium iodide; In dichloromethane; at 45 - 52 ℃; for 6h;

Reference yield:

α-cyclopropylcarbonyl-2-fluorobenzyl chloride (178688-43-2) + 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate (952340-39-5) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (952340-38-4)

Guidance literature:

With triethylamine; In dichloromethane; water; acetonitrile;

upstream raw materials:

α-cyclopropylcarbonyl-2-fluorobenzyl chloride

5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate

tert-butyldimethylsilyl chloride

2-(tert-butyldimethylsilyloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine.p-toluenesulfonate

Downstream raw materials:

prasugel

5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF PRASUGREL HYDROCHLORIDE AND ITS INTERMEDIATES". . . Retrieved 2012/01/14.
• 2、 -. "PRASUGREL SALTS WITH IMPROVED PROPERTIES". Page/Page column 14-15. . Retrieved 2009/10/09.