2-(1-hydroxypropyl)-4-[(tert-butyldimethylsilanyl)oxy]-1-[(4-methylphenyl)sulfonyl]pyrrolidine

Base Information

• Chemical Name: 2-(1-hydroxypropyl)-4-[(tert-butyldimethylsilanyl)oxy]-1-[(4-methylphenyl)sulfonyl]pyrrolidine
• CAS No.: 916588-52-8
• Molecular Formula: C₂₀H₃₅NO₄SSi
• Molecular Weight: 413.654

Synonyms:2-(1-hydroxypropyl)-4-[(tert-butyldimethylsilanyl)oxy]-1-[(4-methylphenyl)sulfonyl]pyrrolidine

Chemical Property of 2-(1-hydroxypropyl)-4-[(tert-butyldimethylsilanyl)oxy]-1-[(4-methylphenyl)sulfonyl]pyrrolidine

Chemical Property:

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Technology Process of 2-(1-hydroxypropyl)-4-[(tert-butyldimethylsilanyl)oxy]-1-[(4-methylphenyl)sulfonyl]pyrrolidine

There total 2 articles about 2-(1-hydroxypropyl)-4-[(tert-butyldimethylsilanyl)oxy]-1-[(4-methylphenyl)sulfonyl]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:

(2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine (261157-02-2) → 2-(1-hydroxypropyl)-4-[(tert-butyldimethylsilanyl)oxy]-1-[(4-methylphenyl)sulfonyl]pyrrolidine (916588-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

2: 372 mg / tetrahydrofuran / -78 - 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxydation / 2: Grignard addition;

DOI:10.1016/j.tet.2006.09.004

Reference yield:

ethylmagnesium bromide (925-90-6) + (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde (863396-18-3) → 2-(1-hydroxypropyl)-4-[(tert-butyldimethylsilanyl)oxy]-1-[(4-methylphenyl)sulfonyl]pyrrolidine (916588-52-8)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.tet.2006.09.004

Reference yield: 86.0%

2-(1-hydroxypropyl)-4-[(tert-butyldimethylsilanyl)oxy]-1-[(4-methylphenyl)sulfonyl]pyrrolidine (916588-52-8) + benzyl bromide (100-39-0) → (2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine (916588-58-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1016/j.tet.2006.09.004

upstream raw materials:

ethylmagnesium bromide

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

(2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine

Downstream raw materials:

(2S,4R)-2-((R)-1-Benzyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine

2-(1-benzyloxypropyl)-1-[(4-methylphenyl)sulfonyl]pyrrolidin-4-one

(3R,5S)-5-((R)-1-Benzyloxy-propyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

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