(1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Base Information

• Chemical Name: (1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• CAS No.: 1372866-06-2
• Molecular Formula: C₁₇H₂₀N₂O₄
• Molecular Weight: 316.357

Synonyms:(1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Chemical Property of (1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Chemical Property:

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Technology Process of (1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

There total 3 articles about (1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate 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%

(1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate (1372866-15-3) → (1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate (1372866-06-2)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo3003425

Reference yield:

methyl 2-isocyano-3-methylbutyrate (63472-88-8,100101-29-9,40846-66-0) → (1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate (1372866-06-2)

Guidance literature:

Multi-step reaction with 2 steps

1: silver hexafluoroantimonate; (R)-DTBM-segphos(AuCl); triethylamine / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

2: sodium tetrahydroborate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; silver hexafluoroantimonate; (R)-DTBM-segphos(AuCl); triethylamine; In tetrahydrofuran;

DOI:10.1021/jo3003425

Reference yield:

N-phenyl-maleimide (941-69-5) → (1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate (1372866-06-2)

Guidance literature:

Multi-step reaction with 2 steps

1: silver hexafluoroantimonate; (R)-DTBM-segphos(AuCl); triethylamine / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

2: sodium tetrahydroborate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; silver hexafluoroantimonate; (R)-DTBM-segphos(AuCl); triethylamine; In tetrahydrofuran;

DOI:10.1021/jo3003425

upstream raw materials:

N-phenyl-maleimide

(1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate

methyl 2-isocyano-3-methylbutyrate

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