ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine

Base Information

• Chemical Name: ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine
• CAS No.: 152955-42-5
• Molecular Formula: C₁₃H₁₉NO₄S
• Molecular Weight: 285.364
• Mol file: 152955-42-5.mol

Synonyms:ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine

Chemical Property of ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine

There total 1 articles about ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine 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: 16.0%

(3R,4S)-1-(4-toluenesulfonyl)-3-methyl-4-hydroxy-2-pyrrolidinecarboxylic acid ethyl ester → ethyl (2S,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine (152955-41-4) + ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine (152955-42-5)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

DOI:10.1002/jhet.5570300241

Reference yield: 94.0%

p-toluenesulfonyl chloride (98-59-9) + ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine (152955-42-5) → (2R,3R,4S)-1-(4-toluenesulfonyl)-2-(4-toluenesulfonyloxymethyl)-3-methyl-4-(4-toluenesulfonyloxy)pyrrolidine (152955-44-7)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1002/jhet.5570300241 DOI:10.1016/0223-5234(93)90013-5

Reference yield:

ethyl (2R,3R,4S)-1-(4-tolylsulfonyl)-3-methyl-4-hydroxy-2-hydroxymethylpyrrolidine (152955-42-5) → (1R,4R,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane (153061-75-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / Ambient temperature

2: 86 percent / xylene / 12 h / Heating

With pyridine; In xylene;

DOI:10.1016/0223-5234(93)90013-5

Downstream raw materials:

(2R,3R,4S)-1-(4-toluenesulfonyl)-2-(4-toluenesulfonyloxymethyl)-3-methyl-4-(4-toluenesulfonyloxy)pyrrolidine

(1R,4R,7S)-2-(4-toluenesulfonyl)-5-phenylmethyl-7-methyl-2,5-diazabicyclo<2.2.1>heptane

ethyl 7-<(1R,4R,7S)-7-methyl-5-phenylmethyl-2,5-diazabicyclo<2.2.1>heptan-2-yl>-6-fluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate