methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate
• CAS No.: 81519-89-3
• Molecular Formula: C₁₃H₁₈N₂O₄S
• Molecular Weight: 298.363
• Mol file: 81519-89-3.mol

Synonyms:methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate

Chemical Property of methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate

There total 9 articles about methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate 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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate (81519-89-3)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 12 h / 0 - 20 °C

2: triethylamine / 12 h / 0 °C

3: sodium azide / N,N-dimethyl-formamide / 60 - 65 °C

4: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C / 760.05 Torr

With sodium azide; palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2013.12.025

Reference yield:

methyl (2S,4S)-4-azido-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate (20275-13-2) → methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate (81519-89-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 4h; under 760 Torr;

DOI:10.1016/S0031-9422(99)00507-5

Reference yield:

methyl (2S,4R)-4-hydroxy-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate (16257-57-1) → methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate (81519-89-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 400 mg

2: 200 mg / NaN₃

3: 7 mg / H₂ / Pd/C / methanol / 4 h / 20 °C / 760 Torr

With sodium azide; hydrogen; palladium on activated charcoal; In methanol; 1: Tosylation / 2: Substitution / 3: Catalytic hydrogenation;

DOI:10.1016/S0031-9422(99)00507-5

upstream raw materials:

methyl (2S,4S)-4-azido-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate

N--trans-4-hydroxy-L-proline

methyl (2S,4R)-4-hydroxy-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate

N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester