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

Base Information

Chemical Name:4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-ethoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile
CAS No.:1421375-95-2
Molecular Formula:C₂₂H₃₂ClN₃O₂Si
Molecular Weight:434.053
Hs Code.:

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

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

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

There total 11 articles about 4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-ethoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-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: 67.0%

: 1421375-87-2
4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile

: 75-03-6
ethyl iodide

: 1421375-95-2
4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-ethoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile

Guidance literature:: 4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

ethyl iodide; In tetrahydrofuran; at 0 - 25 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jm5009049

Reference yield: 67.0%

: 1421375-95-2
4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-ethoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

In tetrahydrofuran; at 0 - 20 ℃; for 3h;

Reference yield:

: 1297544-91-2
2-chloro-4-formyl-3-methylbenzonitrile

: 1421375-95-2
4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-ethoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

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

4.2: 3 h / 0 - 25 °C / Inert atmosphere

With oxalyl dichloride; boron trifluoride diethyl etherate; sodium hydride; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2.1: |Swern Oxidation;
DOI:10.1021/jm5009049