1,3-dimethyl-3-(2-((methoxycarbonyl)amino)-5-methoxyphenyl)-2-pyrrolidone

Base Information

• Chemical Name: 1,3-dimethyl-3-(2-((methoxycarbonyl)amino)-5-methoxyphenyl)-2-pyrrolidone
• CAS No.: 102616-04-6
• Molecular Formula: C₁₅H₂₀N₂O₄
• Molecular Weight: 292.335

Synonyms:1,3-dimethyl-3-(2-((methoxycarbonyl)amino)-5-methoxyphenyl)-2-pyrrolidone

Chemical Property of 1,3-dimethyl-3-(2-((methoxycarbonyl)amino)-5-methoxyphenyl)-2-pyrrolidone

Chemical Property:

Purity/Quality:

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Technology Process of 1,3-dimethyl-3-(2-((methoxycarbonyl)amino)-5-methoxyphenyl)-2-pyrrolidone

There total 13 articles about 1,3-dimethyl-3-(2-((methoxycarbonyl)amino)-5-methoxyphenyl)-2-pyrrolidone 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:

1-cyano-5-methoxybenzocyclobutane (1199-31-1) → 1,3-dimethyl-3-(2-((methoxycarbonyl)amino)-5-methoxyphenyl)-2-pyrrolidone (102616-04-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) LDA, hexamethylphosphoric triamide / 1.) THF, -78 deg C, 70 min, 2.) THF, -78 deg C, 1 h

2: 100 percent / KOH / ethanol; H₂O / 11 h / 100 °C

3: 87 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

4: 100 percent / 1,2-dichloro-benzene / 2.5 h / 180 °C

5: 14.7 g / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

6: 100 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 2 h / -78 °C

7: 97 percent / Jones reagent / 0.33 h / 0 °C

8: 84 percent / sodium chlorite, sulfamic acid / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

9: 1.) diphenylphosphoryl azide, triethylamine / 1.) benzene, reflux, 1 h, 2.) reflux, 3 h

10: 95 percent / Zn-Cu, NH₄Cl / ethanol; H₂O / 8 h / Heating

11: 79 percent / pyridinium dichromate / dimethylformamide / 22 h / Ambient temperature

12: 1.) sodium metaperiodate, osmium tetraoxide, 2.) methylamine hydrochloride, NaCNBH₃ / 1.) Et₂O, water, RT, 2 h, 2.) MeOH, RT, 7 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium hydroxide; sodium chlorite; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; jones reagent; diphenylphosphoranyl azide; aminosulfonic acid; methylamine hydrochloride; copper; sodium cyanoborohydride; ammonium chloride; triethylamine; dicyclohexyl-carbodiimide; zinc; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1,2-dichloro-benzene; tert-butyl alcohol;

DOI:10.1021/jo00365a029

Reference yield:

1-cyano-1,2-dihydro-5-methoxy-1-methylbenzocyclobutene (62562-24-7) → 1,3-dimethyl-3-(2-((methoxycarbonyl)amino)-5-methoxyphenyl)-2-pyrrolidone (102616-04-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / KOH / ethanol; H₂O / 11 h / 100 °C

2: 87 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

3: 100 percent / 1,2-dichloro-benzene / 2.5 h / 180 °C

4: 14.7 g / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

5: 100 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 2 h / -78 °C

6: 97 percent / Jones reagent / 0.33 h / 0 °C

7: 84 percent / sodium chlorite, sulfamic acid / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

8: 1.) diphenylphosphoryl azide, triethylamine / 1.) benzene, reflux, 1 h, 2.) reflux, 3 h

9: 95 percent / Zn-Cu, NH₄Cl / ethanol; H₂O / 8 h / Heating

10: 79 percent / pyridinium dichromate / dimethylformamide / 22 h / Ambient temperature

11: 1.) sodium metaperiodate, osmium tetraoxide, 2.) methylamine hydrochloride, NaCNBH₃ / 1.) Et₂O, water, RT, 2 h, 2.) MeOH, RT, 7 h

With dmap; potassium hydroxide; sodium chlorite; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; jones reagent; diphenylphosphoranyl azide; aminosulfonic acid; methylamine hydrochloride; copper; sodium cyanoborohydride; ammonium chloride; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1,2-dichloro-benzene; tert-butyl alcohol;

DOI:10.1021/jo00365a029

Reference yield:

1,2-dihydro-5-methoxy-1-methylbenzocyclobutene (71644-63-8) → 1,3-dimethyl-3-(2-((methoxycarbonyl)amino)-5-methoxyphenyl)-2-pyrrolidone (102616-04-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 87 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

2: 100 percent / 1,2-dichloro-benzene / 2.5 h / 180 °C

3: 14.7 g / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

4: 100 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 2 h / -78 °C

5: 97 percent / Jones reagent / 0.33 h / 0 °C

6: 84 percent / sodium chlorite, sulfamic acid / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

7: 1.) diphenylphosphoryl azide, triethylamine / 1.) benzene, reflux, 1 h, 2.) reflux, 3 h

8: 95 percent / Zn-Cu, NH₄Cl / ethanol; H₂O / 8 h / Heating

9: 79 percent / pyridinium dichromate / dimethylformamide / 22 h / Ambient temperature

10: 1.) sodium metaperiodate, osmium tetraoxide, 2.) methylamine hydrochloride, NaCNBH₃ / 1.) Et₂O, water, RT, 2 h, 2.) MeOH, RT, 7 h

With dmap; sodium chlorite; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; jones reagent; diphenylphosphoranyl azide; aminosulfonic acid; methylamine hydrochloride; copper; sodium cyanoborohydride; ammonium chloride; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1,2-dichloro-benzene; tert-butyl alcohol;

DOI:10.1021/jo00365a029

upstream raw materials:

3-allyl-1-carbomethoxy-5-methoxy-3-methyloxindole

1-cyano-5-methoxybenzocyclobutane

1,2-dihydro-5-methoxy-1-methylbenzocyclobutene

1-cyano-1,2-dihydro-5-methoxy-1-methylbenzocyclobutene

Downstream raw materials:

1,3-dimethyl-3-(2'-amino-5'-methoxyphenyl)pyrrolidin-2-one

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