1'-benzyl-1,2'-dimethyl-5'-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-2-carbonitrile

Base Information

Chemical Name:1'-benzyl-1,2'-dimethyl-5'-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-2-carbonitrile
CAS No.:287199-81-9
Molecular Formula:C₂₁H₂₁N₃O
Molecular Weight:331.417
Hs Code.:

Synonyms:1'-benzyl-1,2'-dimethyl-5'-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-2-carbonitrile

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Chemical Property of 1'-benzyl-1,2'-dimethyl-5'-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-2-carbonitrile

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Technology Process of 1'-benzyl-1,2'-dimethyl-5'-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-2-carbonitrile

There total 9 articles about 1'-benzyl-1,2'-dimethyl-5'-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-2-carbonitrile 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: 53.0%

: 287199-79-5
N-(2-bromo-benzyl)-2-(2-cyano-1-methyl-1H-indol-3-yl)-N-ethyl-acetamide

: 287199-81-9
1'-benzyl-1,2'-dimethyl-5'-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-2-carbonitrile

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In various solvent(s); at 170 ℃;
DOI:10.1021/ol0061642

Reference yield:

: 87-51-4
indole-3-acetic acid

: 287199-81-9
1'-benzyl-1,2'-dimethyl-5'-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-2-carbonitrile

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / SOCl₂ / 12 h / -78 - 25 °C

2: 92 percent / NaH / tetrahydrofuran / 0 °C

3: 50 percent / POCl₃ / 40 °C

4: 95 percent / NH₂OH*HCl; pyridine / ethanol / 4 h / Heating

5: 72 percent / NEt₃ / acetic anhydride / 4 h / Heating

6: 97 percent / LiOH*H₂O / 2-methyl-propan-2-ol; H₂O / 24 h / 25 °C

7: (COCl)2 / tetrahydrofuran / 0 °C

8: diisopropylethylamine / CH₂Cl₂ / 0 °C

9: 53 percent / Bu₃SnH; AIBN / various solvent(s) / 170 °C

With pyridine; lithium hydroxide; thionyl chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; water; acetic anhydride; tert-butyl alcohol; 1: Esterification / 2: Methylation / 3: Formylation / 4: Condensation / 5: Dehydration / 6: Hydrolysis / 7: Substitution / 8: Substitution / 9: Cyclization;
DOI:10.1021/ol0061642

Reference yield:

: 1912-33-0
Indole-3-acetic acid methyl ester

: 287199-81-9
1'-benzyl-1,2'-dimethyl-5'-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-2-carbonitrile

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / NaH / tetrahydrofuran / 0 °C

2: 50 percent / POCl₃ / 40 °C

3: 95 percent / NH₂OH*HCl; pyridine / ethanol / 4 h / Heating

4: 72 percent / NEt₃ / acetic anhydride / 4 h / Heating

5: 97 percent / LiOH*H₂O / 2-methyl-propan-2-ol; H₂O / 24 h / 25 °C

6: (COCl)2 / tetrahydrofuran / 0 °C

7: diisopropylethylamine / CH₂Cl₂ / 0 °C

8: 53 percent / Bu₃SnH; AIBN / various solvent(s) / 170 °C

With pyridine; lithium hydroxide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; water; acetic anhydride; tert-butyl alcohol; 1: Methylation / 2: Formylation / 3: Condensation / 4: Dehydration / 5: Hydrolysis / 6: Substitution / 7: Substitution / 8: Cyclization;
DOI:10.1021/ol0061642