(S)-(-)-tert-butyl 4,4-bisbenzyl-2-[((4-methylphenyl)sulfonyloxy)methyl]pyrrolidinecarboxylate

Base Information

• Chemical Name: (S)-(-)-tert-butyl 4,4-bisbenzyl-2-[((4-methylphenyl)sulfonyloxy)methyl]pyrrolidinecarboxylate
• CAS No.: 212890-92-1
• Molecular Formula: C₃₁H₃₇NO₅S
• Molecular Weight: 535.704
• Mol file: 212890-92-1.mol

Synonyms:(S)-(-)-tert-butyl 4,4-bisbenzyl-2-[((4-methylphenyl)sulfonyloxy)methyl]pyrrolidinecarboxylate

Chemical Property of (S)-(-)-tert-butyl 4,4-bisbenzyl-2-[((4-methylphenyl)sulfonyloxy)methyl]pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(-)-tert-butyl 4,4-bisbenzyl-2-[((4-methylphenyl)sulfonyloxy)methyl]pyrrolidinecarboxylate

There total 6 articles about (S)-(-)-tert-butyl 4,4-bisbenzyl-2-[((4-methylphenyl)sulfonyloxy)methyl]pyrrolidinecarboxylate 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: 75.0%

p-toluenesulfonyl chloride (98-59-9) + (S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate (212890-91-0) → (S)-(-)-tert-butyl 4,4-bisbenzyl-2-[((4-methylphenyl)sulfonyloxy)methyl]pyrrolidinecarboxylate (212890-92-1)

Guidance literature:

In pyridine; dichloromethane; at -2 ℃; for 16h;

DOI:10.1016/S0040-4020(98)00485-2

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-(-)-tert-butyl 4,4-bisbenzyl-2-[((4-methylphenyl)sulfonyloxy)methyl]pyrrolidinecarboxylate (212890-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

2: 75 percent / CH₂Cl₂; pyridine / 16 h / -2 °C

With triethylamine; In pyridine; dichloromethane; 1: Carboxylation / 2: Tosylation;

DOI:10.1016/S0040-4020(98)00485-2

Reference yield:

benzyl bromide (100-39-0) → (S)-(-)-tert-butyl 4,4-bisbenzyl-2-[((4-methylphenyl)sulfonyloxy)methyl]pyrrolidinecarboxylate (212890-92-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / LDA; HMPA / tetrahydrofuran / 5.5 h / -78 °C

2: 97 percent / p-TsOH / methanol / 1 h / Heating

3: 95 percent / LiAlH₄ / tetrahydrofuran / 96 h / 0 - 20 °C

4: 84 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

5: 75 percent / CH₂Cl₂; pyridine / 16 h / -2 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; dichloromethane; 1: Alkylation / 2: Ring cleavage / 3: Reduction / 4: Carboxylation / 5: Tosylation;

DOI:10.1016/S0040-4020(98)00485-2

upstream raw materials:

p-toluenesulfonyl chloride

(S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate

di-tert-butyl dicarbonate

benzyl bromide

Downstream raw materials:

(S)-(-)-1-[4,4-bisbenzyl-2-((diphenylphosphino)methyl)pyrrolidinyl]-2,2-dimethylpropan-1-one

(S)-(-)-tert-butyl 4,4-bisbenzyl-2-[(diphenylphosphino)methyl]pyrrolidinecarboxylate