(S)-1-tert-butyldimethylsilyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitrovinyl)-2-oxindole

Base Information

Chemical Name:(S)-1-tert-butyldimethylsilyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitrovinyl)-2-oxindole
CAS No.:222533-51-9
Molecular Formula:C₂₂H₃₂N₂O₄Si
Molecular Weight:416.593
Hs Code.:

Synonyms:(S)-1-tert-butyldimethylsilyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitrovinyl)-2-oxindole

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Chemical Property of (S)-1-tert-butyldimethylsilyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitrovinyl)-2-oxindole

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Technology Process of (S)-1-tert-butyldimethylsilyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitrovinyl)-2-oxindole

There total 1 articles about (S)-1-tert-butyldimethylsilyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitrovinyl)-2-oxindole 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:

: 7699-18-5
5-methoxyindolin-2-one

: 222533-51-9
(S)-1-tert-butyldimethylsilyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitrovinyl)-2-oxindole

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 -> -30 deg C, 2 h

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

3: 1.) n-BuLi / 1.) toluene, ether, hexane, -78 -> 0 deg C, 2.) toluene, ether, hexane, -78 -> -10 deg C

With 2,6-dimethylpyridine; n-butyllithium; In dichloromethane;
DOI:10.1021/jo981577q

Reference yield:

: 222533-51-9
(S)-1-tert-butyldimethylsilyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitrovinyl)-2-oxindole

: 1-benzyl-5-methoxy-1H-spiro[indole-3,3'-pyrrolidin]-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / HCl / methanol

2: 97 percent / NaBH₄ / dioxane; methanol / 1 h

3: 1.) NaH / 1.) DMF, mineral oil, room temperature, 30 min, 2.) DMF, mineral oil, 0 deg C, 5 h

4: 80 percent / sodium nitrite, acetic acid / dimethylsulfoxide / 8 h / 37 °C

5: 1.) triethylamine, diphenylphosphoryl azide / 1.) toluene, reflux, 2 h, 2.) toluene, reflux, 12 h

6: 1.) ozone, 2.) dimethyl sulfide / 1.) ethanol, -78 deg C, 2.) ethanol, room temperature, overnight

7: NaBH₄ / methanol / 1 h

8: triethylamine / CH₂Cl₂ / 1 h / 0 °C

9: NaH / tetrahydrofuran; paraffin / 10 h / Ambient temperature

10: hydrogen / Pd/C / methanol / 8 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; dimethylsulfide; diphenylphosphoranyl azide; hydrogen; sodium hydride; ozone; acetic acid; triethylamine; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; paraffin;
DOI:10.1021/jo981577q

Reference yield:

: 222533-51-9
(S)-1-tert-butyldimethylsilyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitrovinyl)-2-oxindole

: 222533-59-7
(R)-1-benzyl-1'-methyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine)

Guidance literature:: Multi-step reaction with 11 steps

1: 95 percent / HCl / methanol

2: 97 percent / NaBH₄ / dioxane; methanol / 1 h

3: 1.) NaH / 1.) DMF, mineral oil, room temperature, 30 min, 2.) DMF, mineral oil, 0 deg C, 5 h

4: 80 percent / sodium nitrite, acetic acid / dimethylsulfoxide / 8 h / 37 °C

5: 1.) triethylamine, diphenylphosphoryl azide / 1.) toluene, reflux, 2 h, 2.) toluene, reflux, 12 h

6: 1.) ozone, 2.) dimethyl sulfide / 1.) ethanol, -78 deg C, 2.) ethanol, room temperature, overnight

7: NaBH₄ / methanol / 1 h

8: triethylamine / CH₂Cl₂ / 1 h / 0 °C

9: NaH / tetrahydrofuran; paraffin / 10 h / Ambient temperature

10: hydrogen / Pd/C / methanol / 8 h / Ambient temperature

11: 1.) NaCNBH₃, 2.) acetic acid / 1.) acetonitrile, water, 15 min, 2.) acetonitrile, water, 1 h

With hydrogenchloride; sodium tetrahydroborate; dimethylsulfide; diphenylphosphoranyl azide; hydrogen; sodium hydride; sodium cyanoborohydride; ozone; acetic acid; triethylamine; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; paraffin;
DOI:10.1021/jo981577q