N-(p-toluenesulfonyl)-cis-3-methylproline

Base Information

• Chemical Name: N-(p-toluenesulfonyl)-cis-3-methylproline
• CAS No.: 76318-74-6
• Molecular Formula: C₁₃H₁₇NO₄S
• Molecular Weight: 283.348
• Mol file: 76318-74-6.mol

Synonyms:

Chemical Property of N-(p-toluenesulfonyl)-cis-3-methylproline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(p-toluenesulfonyl)-cis-3-methylproline

There total 3 articles about N-(p-toluenesulfonyl)-cis-3-methylproline 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: 84.0%

N-(p-toluenesulfonyl)-cis-3-methylprolinol (76251-47-3) → N-(p-toluenesulfonyl)-cis-3-methylproline (76318-74-6,3253-26-7,33443-67-3,76318-76-8,83434-52-0,83434-53-1)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In water; acetone; for 1.5h;

DOI:10.1021/jo00318a042

Reference yield:

2,2-diethyl 3-methyl-5-oxopyrrolidine-2,2-dicarboxylate (2446-12-0) → N-(p-toluenesulfonyl)-cis-3-methylproline (76318-74-6,3253-26-7,33443-67-3,76318-76-8,83434-52-0,83434-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1N sodium hydroxide / 1.) ethanol, 24 deg C, 16 h, 2.) 150 deg C, 0.5 h

2: 1. lithium aluminium hydride / 1.) Tetrahydrofuran, reflux, 18 h; 2.) acetone, 2 h

3: 84 percent / chromium trioxide, sulfuric acid / H₂O; acetone / 1.5 h

With chromium(VI) oxide; sodium hydroxide; lithium aluminium tetrahydride; sulfuric acid; In water; acetone;

DOI:10.1021/jo00318a042

Reference yield:

ethyl cis-3-methylpyroglutamate (76318-70-2) → N-(p-toluenesulfonyl)-cis-3-methylproline (76318-74-6,3253-26-7,33443-67-3,76318-76-8,83434-52-0,83434-53-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1. lithium aluminium hydride / 1.) Tetrahydrofuran, reflux, 18 h; 2.) acetone, 2 h

2: 84 percent / chromium trioxide, sulfuric acid / H₂O; acetone / 1.5 h

With chromium(VI) oxide; lithium aluminium tetrahydride; sulfuric acid; In water; acetone;

DOI:10.1021/jo00318a042

upstream raw materials:

N-(p-toluenesulfonyl)-cis-3-methylprolinol

2,2-diethyl 3-methyl-5-oxopyrrolidine-2,2-dicarboxylate

ethyl cis-3-methylpyroglutamate

Downstream raw materials:

(R)-(6-Methoxy-quinolin-4-yl)-((2R,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol; compound with (2S,3R)-3-methyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

N-Ts-D-syn-3-MePro-quinine