3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

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Chemical Name:3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide
CAS No.:1318265-18-7
Molecular Formula:C₂₈H₃₄BrNO₂
Molecular Weight:496.487
Hs Code.:

Synonyms:3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

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Chemical Property of 3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

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Technology Process of 3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

There total 20 articles about 3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide 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: 84.0%

: 1318265-17-6
3-{[(16β,17β)-17-hydroxy-3-(2-hydroxyethyl)estra-1,3,5(10)-trien-16-yl]methyl}benzamide

: 1318265-18-7
3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 ℃; for 1.66667h;

Reference yield:

: 1318265-21-2
(8R,9S,13S,14S)-13-methyl-3-vinyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolane]

: 1318265-18-7
3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

2.2: 17 h / 0 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / water; acetone / 5 h / 20 °C

4.1: potassium hydroxide / ethanol; water / 0.5 h / Reflux

5.1: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 20 °C

6.1: palladium 10% on activated carbon; hydrogen / ethanol / 36 h / 20 °C / Inert atmosphere

7.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 1.7 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; carbon tetrabromide; dimethylsulfide borane complex; palladium 10% on activated carbon; hydrogen; sodium hydride; triphenylphosphine; potassium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil;
DOI:10.1021/ml200093v

Reference yield:

: 1318265-22-3
3-(2-hydroxyethyl)estra-1⁽¹⁰⁾,2,4-trien-17-dioxolane

: 1318265-18-7
3-{[(16β,17β)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

1.2: 17 h / 0 - 20 °C / Inert atmosphere

2.1: hydrogenchloride / water; acetone / 5 h / 20 °C

3.1: potassium hydroxide / ethanol; water / 0.5 h / Reflux

4.1: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 20 °C

5.1: palladium 10% on activated carbon; hydrogen / ethanol / 36 h / 20 °C / Inert atmosphere

6.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 1.7 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; carbon tetrabromide; palladium 10% on activated carbon; hydrogen; sodium hydride; triphenylphosphine; potassium hydroxide; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil;
DOI:10.1021/ml200093v