1-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-(tert-butyldimethylsiloxy)-1,3-butadiene

Base Information

• Chemical Name: 1-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-(tert-butyldimethylsiloxy)-1,3-butadiene
• CAS No.: 192460-78-9
• Molecular Formula: C₂₆H₃₅NOSi
• Molecular Weight: 405.656

Synonyms:1-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-(tert-butyldimethylsiloxy)-1,3-butadiene

Chemical Property of 1-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-(tert-butyldimethylsiloxy)-1,3-butadiene

Chemical Property:

Purity/Quality:

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Technology Process of 1-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-(tert-butyldimethylsiloxy)-1,3-butadiene

There total 2 articles about 1-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-(tert-butyldimethylsiloxy)-1,3-butadiene 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: 100.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 4-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-butene-2-one (192460-77-8) → 1-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-(tert-butyldimethylsiloxy)-1,3-butadiene (192460-78-9)

Guidance literature:

4-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-butene-2-one; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - -30 ℃; for 3h;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; toluene; at -78 - 20 ℃;

DOI:10.1021/ja9921930

Reference yield:

(R,R)-2,5-diphenylpyrrolidine (155155-73-0) → 1-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-(tert-butyldimethylsiloxy)-1,3-butadiene (192460-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / CH₂Cl₂ / 2.5 h / 70 - 80 °C

2.1: KHMDS / toluene; tetrahydrofuran / 3 h / -78 - -30 °C

2.2: 100 percent / toluene; tetrahydrofuran / -78 - 20 °C

With potassium hexamethylsilazane; In tetrahydrofuran; dichloromethane; toluene; 1.1: Condensation / 2.1: Metallation / 2.2: Condensation;

DOI:10.1021/ja9921930

Reference yield: 100.0%

diethyl Fumarate (623-91-6) + 1-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-(tert-butyldimethylsiloxy)-1,3-butadiene (192460-78-9) → (1S,2R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-((2R,5R)-2,5-diphenyl-pyrrolidin-1-yl)-cyclohex-4-ene-1,2-dicarboxylic acid diethyl ester

Guidance literature:

In toluene; at 20 ℃; for 48h;

DOI:10.1021/ja9921930

upstream raw materials:

tert-butyldimethylsilyl chloride

4-[2,5-(R,R)-diphenyl-pyrrolidin-1-yl]-3-butene-2-one

(R,R)-2,5-diphenylpyrrolidine

Downstream raw materials:

(1S,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((2R,5R)-2,5-diphenyl-pyrrolidin-1-yl)-1-methyl-cyclohex-3-enecarbaldehyde

(1R,2R,3R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-((2R,5R)-2,5-diphenyl-pyrrolidin-1-yl)-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester

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