dimethyl (1S,2S,4S,5S)-4-(tert-butyldimethylsilyloxy)-5-(2-chlorophenylamino)cyclohexane-1,2-dicarboxylate

Base Information

• Chemical Name: dimethyl (1S,2S,4S,5S)-4-(tert-butyldimethylsilyloxy)-5-(2-chlorophenylamino)cyclohexane-1,2-dicarboxylate
• CAS No.: 1254946-98-9
• Molecular Formula: C₂₂H₃₄ClNO₅Si
• Molecular Weight: 456.054

Synonyms:dimethyl (1S,2S,4S,5S)-4-(tert-butyldimethylsilyloxy)-5-(2-chlorophenylamino)cyclohexane-1,2-dicarboxylate

Chemical Property of dimethyl (1S,2S,4S,5S)-4-(tert-butyldimethylsilyloxy)-5-(2-chlorophenylamino)cyclohexane-1,2-dicarboxylate

Chemical Property:

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Technology Process of dimethyl (1S,2S,4S,5S)-4-(tert-butyldimethylsilyloxy)-5-(2-chlorophenylamino)cyclohexane-1,2-dicarboxylate

There total 3 articles about dimethyl (1S,2S,4S,5S)-4-(tert-butyldimethylsilyloxy)-5-(2-chlorophenylamino)cyclohexane-1,2-dicarboxylate 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: 85.0%

dimethyl (1S,2S,4S,5S)-4-(2-chlorophenylamino)-5-hydroxycyclohexane-1,2-dicarboxylate (1254946-85-4) + t-butyldimethylsiyl triflate (69739-34-0) → dimethyl (1S,2S,4S,5S)-4-(tert-butyldimethylsilyloxy)-5-(2-chlorophenylamino)cyclohexane-1,2-dicarboxylate (1254946-98-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1016/j.crci.2009.11.004

Reference yield:

C10H14O5 (845870-02-2) → dimethyl (1S,2S,4S,5S)-4-(tert-butyldimethylsilyloxy)-5-(2-chlorophenylamino)cyclohexane-1,2-dicarboxylate (1254946-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: indium(III) bromide / dichloromethane / 2.5 h / 20 °C

2: 2,6-dimethylpyridine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; indium(III) bromide; In dichloromethane;

DOI:10.1016/j.crci.2009.11.004

Reference yield:

o-chloroaniline (95-51-2) → dimethyl (1S,2S,4S,5S)-4-(tert-butyldimethylsilyloxy)-5-(2-chlorophenylamino)cyclohexane-1,2-dicarboxylate (1254946-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: indium(III) bromide / dichloromethane / 2.5 h / 20 °C

2: 2,6-dimethylpyridine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; indium(III) bromide; In dichloromethane;

DOI:10.1016/j.crci.2009.11.004

upstream raw materials:

dimethyl (1S,2S,4S,5S)-4-(2-chlorophenylamino)-5-hydroxycyclohexane-1,2-dicarboxylate

t-butyldimethylsiyl triflate

C₁₀H₁₄O₅

o-chloroaniline

Downstream raw materials:

dimethyl (1S,2S,4S,5S)-4-(1-(2-chlorophenyl)ureido)-5-hydroxycyclohexane-1,2-dicarboxylate

dimethyl (1S,2S,4S,5S)-4-hydroxy-5-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexane-1,2-dicarboxylate

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