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

Base Information

Chemical Name: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
CAS No.:1421375-87-2
Molecular Formula:C₂₀H₂₈ClN₃O₂Si
Molecular Weight:406
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 15 articles about 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 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: 60.0%

: 1421375-85-0
4-((E)-((2R,3S)-3-(tert-butyldimethylsilyloxy)-2-formylpyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile

: 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

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 25 ℃; for 3h; stereospecific reaction; Inert atmosphere;
DOI:10.1021/jm5009049

Reference yield:

: 757247-75-9
2-chloro-4-iodo-3-methylbenzonitrile

: 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

Guidance literature:: Multi-step reaction with 4 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 / 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / -78 - -30 °C

4.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 20 °C

With oxalyl dichloride; boron trifluoride diethyl etherate; isopropylmagnesium chloride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

Reference yield:

: 496841-04-4,1378292-24-0
methyl (2S,3S)-3-hydroxypyrrolidine-2-carboxylate

: 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

Guidance literature:: Multi-step reaction with 7 steps

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

2: 1H-imidazole / dichloromethane / 3 h / 20 °C

3: lithium triethylborohydride / tetrahydrofuran / 5 h / -78 - 20 °C

4: zinc; ammonium chloride / water; methanol / 1.5 h / 20 - 50 °C

5: acetic acid / 3 h / 20 °C

6: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / -78 - -30 °C

7: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 20 °C

With 1H-imidazole; oxalyl dichloride; boron trifluoride diethyl etherate; lithium triethylborohydride; ammonium chloride; acetic acid; dimethyl sulfoxide; triethylamine; zinc; sodium nitrite; In tetrahydrofuran; methanol; dichloromethane; water;