1,1-dimethylethyl (2S,4R)-4-{[(2,5-dibromophenyl)sulfonyl]amino}-2-methyl-1-pyrrolidinecarboxylate

Base Information

• Chemical Name: 1,1-dimethylethyl (2S,4R)-4-{[(2,5-dibromophenyl)sulfonyl]amino}-2-methyl-1-pyrrolidinecarboxylate
• CAS No.: 1123305-82-7
• Molecular Formula: C₁₆H₂₂Br₂N₂O₄S
• Molecular Weight: 498.236
• Mol file: 1123305-82-7.mol

Synonyms:1,1-dimethylethyl (2S,4R)-4-{[(2,5-dibromophenyl)sulfonyl]amino}-2-methyl-1-pyrrolidinecarboxylate

Chemical Property of 1,1-dimethylethyl (2S,4R)-4-{[(2,5-dibromophenyl)sulfonyl]amino}-2-methyl-1-pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl (2S,4R)-4-{[(2,5-dibromophenyl)sulfonyl]amino}-2-methyl-1-pyrrolidinecarboxylate

There total 10 articles about 1,1-dimethylethyl (2S,4R)-4-{[(2,5-dibromophenyl)sulfonyl]amino}-2-methyl-1-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:

1,1-dimethylethyl (2S,4R)-4-amino-2-methyl-1-pyrrolidinecarboxylate (708274-46-8,348165-63-9) + 2,5-dibromobenzenesulfonyl chloride (23886-64-8) → 1,1-dimethylethyl (2S,4R)-4-{[(2,5-dibromophenyl)sulfonyl]amino}-2-methyl-1-pyrrolidinecarboxylate (1123305-82-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 3h;

Reference yield:

1,2-dimethylethyl-(2S,4R)-4-azido-2-methyl-1-pyrrolidinecarboxylate (708274-45-7) → 1,1-dimethylethyl (2S,4R)-4-{[(2,5-dibromophenyl)sulfonyl]amino}-2-methyl-1-pyrrolidinecarboxylate (1123305-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 10% palladium on activated charcoal; hydrogen / methanol

2: triethylamine

With 10% palladium on activated charcoal; hydrogen; triethylamine; In methanol;

DOI:10.1021/ml100212k

Reference yield:

(2R,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (135042-17-0) → 1,1-dimethylethyl (2S,4R)-4-{[(2,5-dibromophenyl)sulfonyl]amino}-2-methyl-1-pyrrolidinecarboxylate (1123305-82-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1H-imidazole

2: lithium borohydride

3: triethylamine

4: lithium triethylborohydride

5: tetrabutyl ammonium fluoride / tetrahydrofuran

6: triethylamine

7: t-butyl ammonium azide / acetonitrile

8: 10% palladium on activated charcoal; hydrogen / methanol

9: triethylamine

With 1H-imidazole; lithium borohydride; 10% palladium on activated charcoal; tetrabutyl ammonium fluoride; hydrogen; lithium triethylborohydride; triethylamine; t-butyl ammonium azide; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/ml100212k

upstream raw materials:

1,1-dimethylethyl (2S,4R)-4-amino-2-methyl-1-pyrrolidinecarboxylate

2,5-dibromobenzenesulfonyl chloride

4-(tert-butyldimethylsilanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

1,1-dimethylethyl (2S,4S)-4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methyl-1-pyrrolidinecarboxylate

Downstream raw materials:

2,5-dibromo-N-[(3R,5S)-1-cyano-5-methyl-3-pyrrolidinyl]benzenesulfonamide

C₁₁H₁₄Br₂N₂O₂S

C₁₉H₂₆Br₂N₂O₄S

C₂₀H₂₈Br₂N₂O₄S