(2S,5S)-5-(but-3-enyl)-2-(2-(trimethylsilyl)-ethynyl)-1-p-toluenesulfonylpyrrolidine

Base Information

Chemical Name:(2S,5S)-5-(but-3-enyl)-2-(2-(trimethylsilyl)-ethynyl)-1-p-toluenesulfonylpyrrolidine
CAS No.:716336-82-2
Molecular Formula:C₂₀H₂₉NO₂SSi
Molecular Weight:375.607
Hs Code.:

Synonyms:(2S,5S)-5-(but-3-enyl)-2-(2-(trimethylsilyl)-ethynyl)-1-p-toluenesulfonylpyrrolidine

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Chemical Property of (2S,5S)-5-(but-3-enyl)-2-(2-(trimethylsilyl)-ethynyl)-1-p-toluenesulfonylpyrrolidine

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Technology Process of (2S,5S)-5-(but-3-enyl)-2-(2-(trimethylsilyl)-ethynyl)-1-p-toluenesulfonylpyrrolidine

There total 12 articles about (2S,5S)-5-(but-3-enyl)-2-(2-(trimethylsilyl)-ethynyl)-1-p-toluenesulfonylpyrrolidine 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: 95.0%

: 75-77-4
chloro-trimethyl-silane

: 716336-75-3
(2S,5S)-5-(but-3-enyl)-2-ethynyl-1-p-toluenesulfonylpyrrolidine

: 716336-82-2
(2S,5S)-5-(but-3-enyl)-2-(2-(trimethylsilyl)-ethynyl)-1-p-toluenesulfonylpyrrolidine

Guidance literature:: (2S,5S)-5-(but-3-enyl)-2-ethynyl-1-p-toluenesulfonylpyrrolidine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

chloro-trimethyl-silane; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
DOI:10.1016/j.tet.2006.05.088

Reference yield:

: 716336-76-4
(S)-5-(3-(benzyloxy)propyl)-2-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydro-2H-pyrrole

: 716336-82-2
(2S,5S)-5-(but-3-enyl)-2-(2-(trimethylsilyl)-ethynyl)-1-p-toluenesulfonylpyrrolidine

Guidance literature:: Multi-step reaction with 10 steps

1.1: 92 percent / hydrogen / PtO₂ / ethanol / 1 h / 20 °C / 760 Torr

2.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

3.1: 95 percent / hydrogen / Pd(OH)2/C / ethanol / 62 h / 20 °C / 760 Torr

4.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5.1: tBuOK / tetrahydrofuran / 0.33 h / 20 °C

5.2: 98 percent / tetrahydrofuran; CH₂Cl₂ / 14 h / 0 °C

6.1: 98 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

7.1: 86 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 96 percent / PPh₃ / CH₂Cl₂ / 1.5 h / 0 °C

9.1: 80 percent / BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.1: BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

10.2: 95 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With dmap; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; triethylamine; triphenylphosphine; platinum(IV) oxide; palladium dihydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; 4.1: Dess-Martin oxidation / 5.2: Wittig reaction / 7.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2006.05.088

Reference yield:

: 916152-63-1
(2R,5S)-2-(3-Benzyloxy-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidine

: 716336-82-2
(2S,5S)-5-(but-3-enyl)-2-(2-(trimethylsilyl)-ethynyl)-1-p-toluenesulfonylpyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

2.1: 95 percent / hydrogen / Pd(OH)2/C / ethanol / 62 h / 20 °C / 760 Torr

3.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4.1: tBuOK / tetrahydrofuran / 0.33 h / 20 °C

4.2: 98 percent / tetrahydrofuran; CH₂Cl₂ / 14 h / 0 °C

5.1: 98 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

6.1: 86 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

7.1: 96 percent / PPh₃ / CH₂Cl₂ / 1.5 h / 0 °C

8.1: 80 percent / BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

9.1: BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

9.2: 95 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With dmap; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; 3.1: Dess-Martin oxidation / 4.2: Wittig reaction / 6.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2006.05.088