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

Base Information

Chemical Name:(R)-1-benzyl-1'-methyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine)
CAS No.:222533-59-7
Molecular Formula:C₂₀H₂₂N₂O₂
Molecular Weight:322.407
Hs Code.:

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

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Chemical Property of (R)-1-benzyl-1'-methyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine)

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Technology Process of (R)-1-benzyl-1'-methyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine)

There total 27 articles about (R)-1-benzyl-1'-methyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine) 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

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

Guidance literature:: Multi-step reaction with 14 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

4: 95 percent / HCl / methanol

5: 97 percent / NaBH₄ / dioxane; methanol / 1 h

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

7: 80 percent / sodium nitrite, acetic acid / dimethylsulfoxide / 8 h / 37 °C

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

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

10: NaBH₄ / methanol / 1 h

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

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

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

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

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; 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

Reference yield:

: 7135-32-2
1-benzylindolin-2-one

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

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) n-BuLi / 1.) THF, hexane, 2.) THF, hexane

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

3: 97 percent / NaBH₄ / dioxane; methanol

4: 87 percent / sodium nitrite, acetic acid / dimethylsulfoxide

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

6: 1.) ozone, 2.) dimethyl sulfide / 1.) ethanol, -78 deg C, 2.) ethanol, 24 h

7: 47 mg / NaBH₄ / methanol / 1 h

8: 86 percent / triethylsilane, boron trifluoride etherate / CH₂Cl₂ / -78 °C

9: lead tetrakis(trifluoroacetate), trifluoroacetic acid / 1 h / Ambient temperature

10: 1.) NaH / 1.) THF, mineral oil, 0 deg C, 10 min, 2.) THF, mineral oil, room temperature, 30 min

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

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

With triethylsilane; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; Pb(trifluoroacetate)₄; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; hydrogen; sodium hydride; sodium cyanoborohydride; ozone; acetic acid; triethylamine; trifluoroacetic acid; sodium nitrite; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo981577q

Reference yield:

: 222533-60-0
1-benzyl-3-(3-methylbut-2-enyl)-1,3-dihydroindol-2-one

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

2: 97 percent / NaBH₄ / dioxane; methanol

3: 87 percent / sodium nitrite, acetic acid / dimethylsulfoxide

4: 1.) triethylamine, diphenylphosphoryl azide / 1.) toluene, reflux, 2.) toluene, reflux

5: 1.) ozone, 2.) dimethyl sulfide / 1.) ethanol, -78 deg C, 2.) ethanol, 24 h

6: 47 mg / NaBH₄ / methanol / 1 h

7: 86 percent / triethylsilane, boron trifluoride etherate / CH₂Cl₂ / -78 °C

8: lead tetrakis(trifluoroacetate), trifluoroacetic acid / 1 h / Ambient temperature

9: 1.) NaH / 1.) THF, mineral oil, 0 deg C, 10 min, 2.) THF, mineral oil, room temperature, 30 min

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 triethylsilane; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; Pb(trifluoroacetate)₄; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; hydrogen; sodium hydride; sodium cyanoborohydride; ozone; acetic acid; triethylamine; trifluoroacetic acid; sodium nitrite; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo981577q