(3R,1′S,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione

Base Information

Chemical Name:(3R,1′S,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione
CAS No.:1082605-50-2
Molecular Formula:C₁₉H₂₄BrNO₂S
Molecular Weight:410.375
Hs Code.:

Synonyms:(3R,1′S,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione

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Chemical Property of (3R,1′S,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione

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Technology Process of (3R,1′S,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione

There total 4 articles about (3R,1′S,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione 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: 52.0%

: 17642-88-5
1-benzyl-2-pyrrolidinethione

: 1082605-46-6
(S,Z)-4-(2,3-dibromoprop-1-enyl)-2,2-dimethyl-1,3-dioxolane

: 1082605-52-4
(3S,1′S,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione

: 1082605-48-8
(3S,1′R,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione

: 1082605-50-2
(3R,1′S,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione

Guidance literature:: 1-benzyl-2-pyrrolidinethione; (S,Z)-4-(2,3-dibromoprop-1-enyl)-2,2-dimethyl-1,3-dioxolane; In acetonitrile; for 96h; Molecular sieve;

With triethylamine; In acetonitrile; at 35 ℃; for 7h;
DOI:10.1055/s-2008-1078030

Reference yield:

: 182969-96-6
(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate

: 1082605-50-2
(3R,1′S,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 6 h / -78 °C

2.1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 24 h / 0 - 20 °C

3.1: acetonitrile / 96 h / Molecular sieve; Inert atmosphere

3.2: 7 h / 35 - 40 °C / Molecular sieve; Inert atmosphere

With N-Bromosuccinimide; diisobutylaluminium hydride; triphenylphosphine; In dichloromethane; toluene; acetonitrile; 3.1: |Thio-Claisen Rearrangement / 3.2: |Thio-Claisen Rearrangement;
DOI:10.1039/c3ob41580e

Reference yield:

: 1082605-45-5
(S,Z)-2-bromo-3-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

: 1082605-50-2
(3R,1′S,4″S)-1-benzyl-3-[2-bromo-1-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl]pyrrolidine-2-thione

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 3 h / 0 - 20 °C

2.1: acetonitrile / 96 h / Molecular sieve; Inert atmosphere

2.2: 7 h / 35 - 40 °C / Molecular sieve; Inert atmosphere

With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; acetonitrile; 2.1: |Thio-Claisen Rearrangement / 2.2: |Thio-Claisen Rearrangement;
DOI:10.1039/c3ob41580e