4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile

Base Information

• Chemical Name: 4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile
• CAS No.: 1421375-84-9
• Molecular Formula: C₂₀H₃₀ClN₃O₂Si
• Molecular Weight: 408.016
• Mol file: 1421375-84-9.mol

Synonyms:4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile

Chemical Property of 4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile

There total 6 articles about 4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile 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: 44.0%

2-chloro-4-formyl-3-methylbenzonitrile (1297544-91-2) + ((2S,4R)-1-amino-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-yl)methanol (1421375-82-7) → 4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile (1421375-84-9)

Guidance literature:

With acetic acid; at 25 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm5009049

Reference yield:

(R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → 4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile (1421375-84-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium nitrite; acetic acid / water / 4 h / 0 °C / Inert atmosphere

2: 1H-imidazole / dichloromethane / 25 °C / Inert atmosphere

3: lithium triethylborohydride / tetrahydrofuran / 5 h / -78 - 25 °C / Inert atmosphere

4: zinc; ammonium chloride; water / methanol / 1.5 h / 0 - 50 °C / Inert atmosphere

5: acetic acid / 3 h / 25 °C / Inert atmosphere

With 1H-imidazole; water; lithium triethylborohydride; ammonium chloride; acetic acid; zinc; sodium nitrite; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jm5009049

Reference yield:

(2S,4R)-methyl-4-hydroxy-1-nitrosopyrrolidine-2-carboxylate (60096-51-7) → 4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile (1421375-84-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1H-imidazole / dichloromethane / 25 °C / Inert atmosphere

2: lithium triethylborohydride / tetrahydrofuran / 5 h / -78 - 25 °C / Inert atmosphere

3: zinc; ammonium chloride; water / methanol / 1.5 h / 0 - 50 °C / Inert atmosphere

4: acetic acid / 3 h / 25 °C / Inert atmosphere

With 1H-imidazole; water; lithium triethylborohydride; ammonium chloride; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm5009049

upstream raw materials:

2-chloro-4-formyl-3-methylbenzonitrile

((2S,4R)-1-amino-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-yl)methanol

(R)-4-hydroxy-L-proline ethyl ester

(2S,4R)-methyl-4-hydroxy-1-nitrosopyrrolidine-2-carboxylate

Downstream raw materials:

4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-formylpyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile

4-((3S,3aR,5R)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile

4-((3S,3aR,5R)-5-(tert-butyldimethylsilyloxy)-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile

2-chloro-4-((3S,3aS,5R)-5-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile