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

Base Information

• Chemical Name: 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
• CAS No.: 1421375-33-8
• Molecular Formula: C₁₅H₁₆ClN₃O₂
• Molecular Weight: 305.764
• Mol file: 1421375-33-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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: 69.0%

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 (1421375-98-5) → 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 (1421375-33-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 25 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm5009049

Reference yield:

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 (1421375-88-3) → 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 (1421375-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 - 25 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 25 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jm5009049

Reference yield:

2-chloro-4-iodo-3-methylbenzonitrile (757247-75-9) → 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 (1421375-33-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / 2 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

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

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.2: 2 h / 0 - 25 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 25 °C / Inert atmosphere

With oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; sodium hydride; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane; 3.1: |Swern Oxidation;

DOI:10.1021/jm5009049

upstream raw materials:

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-iodo-3-methylbenzonitrile

2-chloro-4-formyl-3-methylbenzonitrile

Downstream raw materials:

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

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

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

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