16β-Fluoro-3-methoxy-1,3,5(10)-estratrien-17-one

Base Information

• Chemical Name: 16β-Fluoro-3-methoxy-1,3,5(10)-estratrien-17-one
• CAS No.: 2383-29-1
• Molecular Weight: 302.38
• Mol file: 2383-29-1.mol

Synonyms:16β-Fluoro-3-methoxy-1,3,5(10)-estratrien-17-one

Chemical Property of 16β-Fluoro-3-methoxy-1,3,5(10)-estratrien-17-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 16β-Fluoro-3-methoxy-1,3,5(10)-estratrien-17-one

There total 9 articles about 16β-Fluoro-3-methoxy-1,3,5(10)-estratrien-17-one 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: 93.0%

(8R,9S,13S,14S)-16-Fluoro-3-methoxy-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-16-carboxylic acid allyl ester (122618-01-3) → 16β-Fluor-3-methoxy-oestratrien-(1,3,5(10))-on-(17) (2383-29-1)

Guidance literature:

With formic acid; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In 1,4-dioxane; Heating;

DOI:10.1246/cl.1999.577

Reference yield: 83.0%

16β-allyloxycarbonyl-16α-fluoroestrone methyl ether (155528-44-2) → 16β-Fluor-3-methoxy-oestratrien-(1,3,5(10))-on-(17) (2383-29-1)

Guidance literature:

With formic acid; triethylamine; tris(dibenzylideneacetone)dipalladium chloroform complex; triphenylphosphine; In 1,4-dioxane; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80770-5

Reference yield:

(8R,9S,13S,14S)-3-Methoxy-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-16-carboxylic acid allyl ester (122618-00-2) → 16β-Fluor-3-methoxy-oestratrien-(1,3,5(10))-on-(17) (2383-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / NaH, N-fluoro-2,4,6-trimethylpyridinium triflate / tetrahydrofuran / 2 h / 0 °C

2: 83 percent / HCOOH, Et₃N / Pd(dba)3CHCl₃*PPh₃ / dioxane / 24 h / Ambient temperature

With formic acid; sodium hydride; 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate; triethylamine; tris(dibenzylideneacetone)dipalladium chloroform complex; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0040-4020(01)80770-5

upstream raw materials:

16α-iodo-3-methoxy-estra-1,3,5(10)-trien-17-one

3-Methoxy-17-acetoxy-1,3,5⁽¹⁰⁾,16-estratetraene

(8R,9S,13S,14S)-16-Fluoro-3-methoxy-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-16-carboxylic acid allyl ester

16β-allyloxycarbonyl-16α-fluoroestrone methyl ether

Refernces

• 1、 Poss, A. J.,Puy, M. Van Der,Nalewajek, D.,Shia, G. A.,Wagner, W. J.,Frenette, R. L.. "N-Fluoropyridinium Pyridine Heptafluorodiborate: A Useful Fluorinating Agent". . p. 5962 - 5964. Retrieved 2007/10/02.