(R)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine

Base Information

• Chemical Name: (R)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine
• CAS No.: 1304754-74-2
• Molecular Formula: C₁₇H₁₆BrF₂NO₂S
• Molecular Weight: 416.286

Synonyms:(R)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine

Chemical Property of (R)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine

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Technology Process of (R)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine

There total 6 articles about (R)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine 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:

methyl-4-bromo-pent-4-enoate (194805-62-4) → (R)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine (1304754-74-2) + (S)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 16 h / 100 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 25 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 0 - 25 °C

4.1: potassium hydroxide / N,N-dimethyl-formamide / 0.5 h / 100 °C

4.2: 1 h / 100 °C

5.1: N-Bromosuccinimide; C₂₉H₃₃N₃O₄S / dichloromethane / 17 h / -78 °C / Inert atmosphere; Darkness

With N-Bromosuccinimide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; C₂₉H₃₃N₃O₄S; sodium carbonate; triethylamine; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja201627h

Reference yield:

3,5-difluoro-N-(4-phenyl-4-pentenyl)benzenesulfonamide (1304753-86-3) → (R)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine (1304754-74-2) + (S)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine

Guidance literature:

With N-Bromosuccinimide; C₂₉H₃₃N₃O₄S; In dichloromethane; at -78 ℃; for 17h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Darkness;

DOI:10.1021/ja201627h

Reference yield:

4-phenylpent-4-en-1-ol (93222-37-8) → (R)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine (1304754-74-2) + (S)-2-(bromomethyl)-1-(3,5-difluorophenylsulfonyl)-2-phenylpyrrolidine

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 0 - 25 °C

2.1: potassium hydroxide / N,N-dimethyl-formamide / 0.5 h / 100 °C

2.2: 1 h / 100 °C

3.1: N-Bromosuccinimide; C₂₉H₃₃N₃O₄S / dichloromethane / 17 h / -78 °C / Inert atmosphere; Darkness

With N-Bromosuccinimide; C₂₉H₃₃N₃O₄S; triethylamine; potassium hydroxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja201627h

upstream raw materials:

3,5-difluoro-N-(4-phenyl-4-pentenyl)benzenesulfonamide

4-phenylpent-4-en-1-ol

4-phenylpent-4-enoic acid methyl ester

methyl-4-bromo-pent-4-enoate

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