rel-(1R,2R)-11-benzyl-10-vinylidene-11-azatricyclo<5.3.2.0^2,7>-4-dodecen-12-one

Base Information

• Chemical Name: rel-(1R,2R)-11-benzyl-10-vinylidene-11-azatricyclo<5.3.2.0^2,7>-4-dodecen-12-one
• CAS No.: 95455-18-8
• Molecular Formula: C₂₀H₂₁NO
• Molecular Weight: 291.393

Synonyms:rel-(1R,2R)-11-benzyl-10-vinylidene-11-azatricyclo<5.3.2.0^2,7>-4-dodecen-12-one

Chemical Property of rel-(1R,2R)-11-benzyl-10-vinylidene-11-azatricyclo<5.3.2.0^2,7>-4-dodecen-12-one

Chemical Property:

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Technology Process of rel-(1R,2R)-11-benzyl-10-vinylidene-11-azatricyclo<5.3.2.0^2,7>-4-dodecen-12-one

There total 5 articles about rel-(1R,2R)-11-benzyl-10-vinylidene-11-azatricyclo<5.3.2.0^2,7>-4-dodecen-12-one 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: 97.0%

rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentynyl>-1-isoindolone (95455-17-7) → rel-(1R,2R)-11-benzyl-10-vinylidene-11-azatricyclo<5.3.2.02,7>-4-dodecen-12-one (95455-18-8)

Guidance literature:

With formic acid; for 0.5h;

DOI:10.1016/S0040-4039(01)91310-3

Reference yield:

cis-2-benzyl-1,3,3a,4,7,7a-hexahydro-1,3-isoindoledione (66050-03-1) → rel-(1R,2R)-11-benzyl-10-vinylidene-11-azatricyclo<5.3.2.02,7>-4-dodecen-12-one (95455-18-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / sodium borohydride, 2 M HCl / 4 h / 0 - 5 °C

2: 55 percent / LDA / tetrahydrofuran / 2 h / -78 - 20 °C

3: 97 percent / formic acid / 0.5 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; formic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)86638-2

Reference yield:

rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-1-isoindolone (95455-15-5) → rel-(1R,2R)-11-benzyl-10-vinylidene-11-azatricyclo<5.3.2.02,7>-4-dodecen-12-one (95455-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / LDA / tetrahydrofuran / 2 h / -78 - 20 °C

2: 97 percent / formic acid / 0.5 h / Ambient temperature

With formic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)86638-2

upstream raw materials:

rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentynyl>-1-isoindolone

cis-2-benzyl-1,3,3a,4,7,7a-hexahydro-1,3-isoindoledione

rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-1-isoindolone

benzyl chloride

Downstream raw materials:

N-benzyl-4-ethylidenecyclohexanecarboxamide

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