17α-HydroxyMethyl-17β-Methyl-18-norandrosta-1,4,13-trien-3-one

Base Information

• Chemical Name: 17α-HydroxyMethyl-17β-Methyl-18-norandrosta-1,4,13-trien-3-one
• CAS No.: 1203575-20-5
• Molecular Formula: C₂₀H₂₆O₂
• Molecular Weight: 298.425
• Mol file: 1203575-20-5.mol

Synonyms:(8R,9S,10R,17R)-17-(hydroxymethyl)-10,17-dimethyl-6,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-3-one;

Chemical Property of 17α-HydroxyMethyl-17β-Methyl-18-norandrosta-1,4,13-trien-3-one

Chemical Property:

• PSA: 37.30000
• LogP: 3.96700

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 17α-Hydroxymethyl-17β-methyl-18-norandrosta-1,4,13-trien-3-one is a urinary metabolite of the human doping Methandienone (Methandrostenolone, M226000).

Technology Process of 17α-HydroxyMethyl-17β-Methyl-18-norandrosta-1,4,13-trien-3-one

There total 19 articles about 17α-HydroxyMethyl-17β-Methyl-18-norandrosta-1,4,13-trien-3-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: 90.0%

17β-acetoxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-on → 18-nor-17β-hydroxymethyl-17α-methylandrost-1,4,13-triene-3-one (912291-78-2,1203575-20-5)

Guidance literature:

With potassium carbonate; In methanol; for 5h;

DOI:10.1002/chem.201602957

Reference yield: 22.0%

spiro(13α-methylandrost-1,4-dien-17,2'-oxirane)-3-one (55706-91-7) → 18-nor-17β-hydroxymethyl-17α-methylandrost-1,4,13-triene-3-one (912291-78-2,1203575-20-5)

Guidance literature:

With phosphoric acid; In water; toluene; Reflux;

DOI:10.1016/j.steroids.2016.08.013

Reference yield:

3β-[(tert-butyldimethylsilyl)oxy]-13α,14α-epoxy-17α-formyl-17β-methyl-18-norandrost-5-ene → 18-nor-17β-hydroxymethyl-17α-methylandrost-1,4,13-triene-3-one (912291-78-2,1203575-20-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dichloromethane / 20 °C / Molecular sieve

1.2: 0.5 h / 20 °C / Molecular sieve

2.1: acetic acid; [bis(acetoxy)iodo]benzene; palladium diacetate / 0.75 h / 100 °C

3.1: methyl trifluoromethanesulfonate / dichloromethane / 2 h

4.1: sodium tetrahydroborate / ethanol / 0.67 h / 0 °C

4.2: 5 h / 20 °C

5.1: zinc trifluoromethanesulfonate / acetonitrile / 4 h

6.1: nickel / water; ethanol; ethyl acetate / 1 h / 80 °C / Inert atmosphere

7.1: tungsten(VI) chloride; n-butyllithium; lithium iodide / hexane; tetrahydrofuran / 0.33 h / -78 - 40 °C / Inert atmosphere

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 °C

8.2: 4 h / 60 °C

9.1: sodium hydrogencarbonate; C₁₃H₁₀O₃Se₂ / toluene / 1.25 h / 100 °C

10.1: potassium carbonate / methanol / 5 h

With sodium tetrahydroborate; n-butyllithium; [bis(acetoxy)iodo]benzene; C₁₃H₁₀O₃Se₂; palladium diacetate; zinc trifluoromethanesulfonate; nickel; tungsten(VI) chloride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; methyl trifluoromethanesulfonate; lithium iodide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; toluene; acetonitrile;

DOI:10.1002/chem.201602957

upstream raw materials:

17,17-dimethyl-18-norandrosta-1,4,13⁽¹⁴⁾-trien-3-one

3β-acetoxy-14α-hydroxyandrost-5-en-17-one

3β,14α-dihydroxy-androst-5-en-17-one