(2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine

Base Information

Chemical Name:(2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine
CAS No.:863396-16-1
Molecular Formula:C₁₉H₃₁NO₃SSi
Molecular Weight:381.612
Hs Code.:

Synonyms:(2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine

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Technology Process of (2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine

There total 7 articles about (2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine 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:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 863396-16-1
(2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / triethylamine / CH₂Cl₂ / 10 h / cooling

2.1: 97 percent / imidazole / dimethylformamide / 2 h / 20 °C

3.1: 95 percent / NaBH₄; LiCl / methanol / 12 h / 20 °C

4.1: oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1.5 h

5.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

5.2: 871 mg / tetrahydrofuran / 8 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Swern oxidation / 5.2: Wittig olefination;
DOI:10.3987/COM-05-10407

Reference yield:

: 2065-66-9
methyl-triphenylphosphonium iodide

: 863396-18-3
(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde

: 863396-16-1
(2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine

Guidance literature:: methyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde; In tetrahydrofuran; at -78 ℃; for 8h;
DOI:10.3987/COM-05-10407

Reference yield:

: 16257-57-1
methyl (2S,4R)-4-hydroxy-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate

: 863396-16-1
(2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: 95 percent / NaBH₄; LiCl / methanol / 12 h / 20 °C

3.1: oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1.5 h

4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

4.2: 871 mg / tetrahydrofuran / 8 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 4.2: Wittig olefination;
DOI:10.3987/COM-05-10407