(2'S)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-hydroxybutan-2'-yl]-1H-pyrrole-2-carbonitrile

Base Information

• Chemical Name: (2'S)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-hydroxybutan-2'-yl]-1H-pyrrole-2-carbonitrile
• CAS No.: 1346162-56-8
• Molecular Formula: C₂₅H₂₈Br₂N₂O₂Si
• Molecular Weight: 576.403
• Mol file: 1346162-56-8.mol

Synonyms:(2'S)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-hydroxybutan-2'-yl]-1H-pyrrole-2-carbonitrile

Chemical Property of (2'S)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-hydroxybutan-2'-yl]-1H-pyrrole-2-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-hydroxybutan-2'-yl]-1H-pyrrole-2-carbonitrile

There total 7 articles about (2'S)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-hydroxybutan-2'-yl]-1H-pyrrole-2-carbonitrile 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:

C25H26Br2N2O2Si → (2'S)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-hydroxybutan-2'-yl]-1H-pyrrole-2-carbonitrile (1346162-56-8)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -40 ℃; for 0.5h; chemoselective reaction; Inert atmosphere;

DOI:10.1039/c1ob06078c

Reference yield:

C25H26Br2N2O2Si → (2'S)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-hydroxybutan-2'-yl]-1H-pyrrole-2-carbonitrile (1346162-56-8) + (2'R)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-hydroxybutan-2'-yl]-1H-pyrrole-2-carbonitrile

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -20 ℃; for 0.5h; chemoselective reaction; Inert atmosphere;

DOI:10.1039/c1ob06078c

Reference yield:

4,5-dibromo-1H-pyrrole-2-carbonitrile (34649-19-9) → (2'S)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-hydroxybutan-2'-yl]-1H-pyrrole-2-carbonitrile (1346162-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; benzoic acid / toluene / 18 h / -40 °C / Inert atmosphere

2: sodium tetrahydroborate / ethanol / 0.5 h / -40 °C / Inert atmosphere

With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; sodium tetrahydroborate; benzoic acid; In ethanol; toluene; 1: aza-Michael addition;

DOI:10.1039/c1ob06078c

upstream raw materials:

(E)-4-(t-butyldiphenylsilyl)oxy-2-butenal

4,5-dibromo-1H-pyrrole-2-carbonitrile

4-(t-butyl-diphenyl-silanyloxy)-but-2-enal

Downstream raw materials:

(2'S)-4,5-dibromo-1-[4'-methoxy-1'-(p-toluenesulfonyloxy)butan-2'-yl]-1H-pyrrole-2-carbonitrile

(2'S)-4,5-dibromo-1-[1'-(tert-butyldiphenylsilyloxy)-4'-methoxybutan-2'-yl]-1H-pyrrole-2-carbonitrile