1-benzyl 2-methyl (2S,3S)-3-((3-nitrophenyl)sulfonyloxy)pyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: 1-benzyl 2-methyl (2S,3S)-3-((3-nitrophenyl)sulfonyloxy)pyrrolidine-1,2-dicarboxylate
• CAS No.: 1194059-14-7
• Molecular Formula: C₂₀H₂₀N₂O₉S
• Molecular Weight: 464.453
• Mol file: 1194059-14-7.mol

Synonyms:1-benzyl 2-methyl (2S,3S)-3-((3-nitrophenyl)sulfonyloxy)pyrrolidine-1,2-dicarboxylate

Chemical Property of 1-benzyl 2-methyl (2S,3S)-3-((3-nitrophenyl)sulfonyloxy)pyrrolidine-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-benzyl 2-methyl (2S,3S)-3-((3-nitrophenyl)sulfonyloxy)pyrrolidine-1,2-dicarboxylate

There total 3 articles about 1-benzyl 2-methyl (2S,3S)-3-((3-nitrophenyl)sulfonyloxy)pyrrolidine-1,2-dicarboxylate 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: 91.0%

3-nitrobenzenesulphonyl chloride (121-51-7) + 1-benzyl 2-methyl(2S,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate → 1-benzyl 2-methyl (2S,3S)-3-((3-nitrophenyl)sulfonyloxy)pyrrolidine-1,2-dicarboxylate (1194059-14-7)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 64h;

DOI:10.1002/cmdc.201700426

Reference yield:

trans-3-hydroxy-L-proline (4298-08-2) → 1-benzyl 2-methyl (2S,3S)-3-((3-nitrophenyl)sulfonyloxy)pyrrolidine-1,2-dicarboxylate (1194059-14-7)

Guidance literature:

Multi-step reaction with 3 steps

1: acetyl chloride / 20 h / 0 - 65 °C

2: sodium hydrogencarbonate / water; tetrahydrofuran / 23 h / 0 - 20 °C

3: pyridine / 64 h / 0 - 20 °C

With pyridine; sodium hydrogencarbonate; acetyl chloride; In tetrahydrofuran; water;

DOI:10.1002/cmdc.201700426

Reference yield:

(2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride (1844898-16-3) → 1-benzyl 2-methyl (2S,3S)-3-((3-nitrophenyl)sulfonyloxy)pyrrolidine-1,2-dicarboxylate (1194059-14-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / tetrahydrofuran; water / 0 - 20 °C / Inert atmosphere

2: pyridine / 64 h / 0 - 20 °C / Inert atmosphere

With pyridine; sodium hydrogencarbonate; In tetrahydrofuran; water;

upstream raw materials:

3-nitrobenzenesulphonyl chloride

trans-3-hydroxy-L-proline

(2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride

Downstream raw materials:

benzyl (2S,3R)-3-[(benzyloxy)carbonyl]amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate

benzyl (2S,3R)-3-((benzyloxy)carbonylamino)-2-(((4-methylphenyl)sulfonyl)oxymethyl)-pyrrolidine-1-carboxylate

benzyl (2R,3R)-3-((benzyloxy)carbonylamino)-2-((tert-butoxycarbonylamino)methyl)-pyrrolidine-1-carboxylate

benzyl (2R,3R)-3-((benzyloxy)carbonylamino)-2-azidomethyl-pyrrolidine-1-carboxylate