tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate
CAS No.:121148-21-8
Molecular Formula:C₁₇H₂₄N₂O₅S
Molecular Weight:368.454
Hs Code.:

Synonyms:tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

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Chemical Property of tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

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Technology Process of tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

There total 11 articles about tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-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: 74.0%

: 121148-18-3
1-tert-butyl 2-methyl (2S,4R)-4-(((4-methylphenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate

: 121148-21-8
tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 5h;
DOI:10.1016/S0968-0896(01)00397-2

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 121148-21-8
tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 53.4 g / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

2: 56.2 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 5 °C

3: 88.7 percent / dimethylsulfoxide / 90 °C

4: 98.4 percent / potassium carbonate / methanol / 1 h / 20 °C

5: 100 percent / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

6: 90.8 percent / sodium azide / dimethylsulfoxide / 90 °C

7: H₂ / 10 percent Pd/C / methanol / 3 h / 20 °C / 2280 Torr

8: 5.38 g / pyridine / 5 h / 0 - 5 °C

9: 74 percent / diisobutylaluminum hydride / toluene / 5 h / -78 °C

With sodium azide; hydrogen; diisobutylaluminium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In pyridine; methanol; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1016/S0968-0896(01)00397-2

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 121148-21-8
tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 53.4 g / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

2: 56.2 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 5 °C

3: 88.7 percent / dimethylsulfoxide / 90 °C

4: 98.4 percent / potassium carbonate / methanol / 1 h / 20 °C

5: 100 percent / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

6: 90.8 percent / sodium azide / dimethylsulfoxide / 90 °C

7: H₂ / 10 percent Pd/C / methanol / 3 h / 20 °C / 2280 Torr

8: 5.38 g / pyridine / 5 h / 0 - 5 °C

9: 74 percent / diisobutylaluminum hydride / toluene / 5 h / -78 °C

With sodium azide; hydrogen; diisobutylaluminium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In pyridine; methanol; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1016/S0968-0896(01)00397-2