(-)dimethyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]methyl malonate

Base Information

• Chemical Name: (-)dimethyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]methyl malonate
• CAS No.: 1289154-17-1
• Molecular Formula: C₁₇H₂₃NO₆S
• Molecular Weight: 369.439
• Mol file: 1289154-17-1.mol

Synonyms:(-)dimethyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]methyl malonate

Chemical Property of (-)dimethyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]methyl malonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)dimethyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]methyl malonate

There total 3 articles about (-)dimethyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]methyl malonate 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: 80.0%

(S)(-)-N,O-bis(p-toluenesulphonyl)-2-hydroxymethyl pyrrolidine (52682-03-8) + malonic acid dimethyl ester (108-59-8) → (-)dimethyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]methyl malonate (1289154-17-1)

Guidance literature:

malonic acid dimethyl ester; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

(S)(-)-N,O-bis(p-toluenesulphonyl)-2-hydroxymethyl pyrrolidine; In N,N-dimethyl-formamide; at 100 ℃; for 8h;

DOI:10.1515/HC.2010.16.2-3.105

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (-)dimethyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]methyl malonate (1289154-17-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / 12 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C

2.2: 8 h / 100 °C

With pyridine; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1515/HC.2010.16.2-3.105

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (-)dimethyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]methyl malonate (1289154-17-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: zinc(II) tetrahydroborate / tetrahydrofuran / 10 h / Heating

2.1: pyridine / 12 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C

3.2: 8 h / 100 °C

With pyridine; zinc(II) tetrahydroborate; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1515/HC.2010.16.2-3.105

upstream raw materials:

(S)(-)-N,O-bis(p-toluenesulphonyl)-2-hydroxymethyl pyrrolidine

malonic acid dimethyl ester

p-toluenesulfonyl chloride

L-proline

Downstream raw materials:

(-)methyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propionate

(-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-acetyl-β-L-fucopyranoside

(-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside

(-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propan-1-ol