(8R,9S,10R,13S,14S,17S)-17-Hydroxy-2-[1-hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-17-(3-trifluoromethyl-phenylethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

Base Information

• Chemical Name: (8R,9S,10R,13S,14S,17S)-17-Hydroxy-2-[1-hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-17-(3-trifluoromethyl-phenylethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
• CAS No.: 143137-32-0
• Molecular Formula: C₂₉H₃₁F₃O₃
• Molecular Weight: 484.559

Synonyms:

Chemical Property of (8R,9S,10R,13S,14S,17S)-17-Hydroxy-2-[1-hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-17-(3-trifluoromethyl-phenylethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

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Technology Process of (8R,9S,10R,13S,14S,17S)-17-Hydroxy-2-[1-hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-17-(3-trifluoromethyl-phenylethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

There total 2 articles about (8R,9S,10R,13S,14S,17S)-17-Hydroxy-2-[1-hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-17-(3-trifluoromethyl-phenylethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-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:

levonorgestrel (434-03-7) → (8R,9S,10R,13S,14S,17S)-17-Hydroxy-2-[1-hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-17-(3-trifluoromethyl-phenylethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (143137-32-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / Et₂NH, CuI / (PPh₃P)2PdCl₂ / tetrahydrofuran / Ambient temperature

2: 1) NaOMe / 1) MeOH, THF, 0 deg C, 10 min, 2) 16h, RT

With copper(l) iodide; sodium methylate; diethylamine; (PPh₃P)2PdCl₂; In tetrahydrofuran;

DOI:10.1055/s-1992-26151

Reference yield:

Methyl formate (107-31-3) + (8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-17-(3-trifluoromethyl-phenylethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (143137-22-8) → (8R,9S,10R,13S,14S,17S)-17-Hydroxy-2-[1-hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-17-(3-trifluoromethyl-phenylethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (143137-32-0)

Guidance literature:

With sodium methylate; Multistep reaction; 1) MeOH, THF, 0 deg C, 10 min, 2) 16h, RT;

DOI:10.1055/s-1992-26151

Reference yield:

(8R,9S,10R,13S,14S,17S)-17-Hydroxy-2-[1-hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-17-(3-trifluoromethyl-phenylethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (143137-32-0) → (1S,3aS,3bR,10aR,10bS,12aS)-10a,12a-Dimethyl-1-(3-trifluoromethyl-phenylethynyl)-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-7-oxa-8-aza-dicyclopenta[a,h]phenanthren-1-ol (143137-26-2)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; acetic acid; In water; for 0.25h; Yield given; Heating;

DOI:10.1055/s-1992-26151

upstream raw materials:

Methyl formate

(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-17-(3-trifluoromethyl-phenylethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

levonorgestrel

Downstream raw materials:

(1S,3aS,3bR,10aR,10bS,12aS)-10a,12a-Dimethyl-1-(3-trifluoromethyl-phenylethynyl)-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-7-oxa-8-aza-dicyclopenta[a,h]phenanthren-1-ol

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