ethyl (2R,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate

Base Information

• Chemical Name: ethyl (2R,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate
• CAS No.: 627100-75-8
• Molecular Formula: C₂₁H₂₅NO₅S
• Molecular Weight: 403.499
• Mol file: 627100-75-8.mol

Synonyms:ethyl (2R,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate

Chemical Property of ethyl (2R,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2R,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate

There total 4 articles about ethyl (2R,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate 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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + (2R,4R)-ethyl N1-benzyl-4-hydroxypyrrolidine-2-carboxylate (171192-72-6) → ethyl (2R,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate (627100-75-8)

Guidance literature:

With pyridine; at 20 ℃; for 48h;

DOI:10.1016/j.tetasy.2003.08.019

Reference yield:

(2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride (77449-99-1) → ethyl (2R,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate (627100-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / CHCl₃ / 6 h / Heating

1.2: 98 percent / aq. NaOH / CHCl₃ / 20 °C

2.1: 100 percent / pyridine / 48 h / 20 °C

With pyridine; triethylamine; In chloroform;

DOI:10.1016/j.tetasy.2003.08.019

Reference yield:

cis-hydroxy-D-proline (2584-71-6,30724-02-8) → ethyl (2R,4R)-1-benzyl-4-(4-methylphenylsulfonyloxy)prolinate (627100-75-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 82 percent / SOCl₂ / 6 h / Heating

2.1: Et₃N / CHCl₃ / 6 h / Heating

2.2: 98 percent / aq. NaOH / CHCl₃ / 20 °C

3.1: 100 percent / pyridine / 48 h / 20 °C

With pyridine; thionyl chloride; triethylamine; In chloroform;

DOI:10.1016/j.tetasy.2003.08.019

upstream raw materials:

p-toluenesulfonyl chloride

(2R,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate

(2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride

cis-hydroxy-D-proline

Downstream raw materials:

(3R,5R)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl tosylate