(1S,3R,4aS,8S,9aR)-11-((benzyloxy)carbonyl)-3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6-carboxylic acid

Base Information

Chemical Name:(1S,3R,4aS,8S,9aR)-11-((benzyloxy)carbonyl)-3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6-carboxylic acid
CAS No.:1448722-47-1
Molecular Formula:C₂₄H₂₉NO₄
Molecular Weight:395.499
Hs Code.:

Synonyms:(1S,3R,4aS,8S,9aR)-11-((benzyloxy)carbonyl)-3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6-carboxylic acid

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Chemical Property of (1S,3R,4aS,8S,9aR)-11-((benzyloxy)carbonyl)-3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6-carboxylic acid

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Technology Process of (1S,3R,4aS,8S,9aR)-11-((benzyloxy)carbonyl)-3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6-carboxylic acid

There total 7 articles about (1S,3R,4aS,8S,9aR)-11-((benzyloxy)carbonyl)-3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6-carboxylic acid 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: 90.0%

: 1448722-46-0
(1S,3R,4aS,8S,9aR)-11-benzyl 6-ethyl 3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6,11-dicarboxylate

: 1448722-47-1
(1S,3R,4aS,8S,9aR)-11-((benzyloxy)carbonyl)-3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6-carboxylic acid

Guidance literature:: With ethanol; sodium hydroxide; at 60 ℃; for 13.5h; Inert atmosphere;
DOI:10.1021/ol401954f

Reference yield:

: (3R,4aS,8aR)-N-benzyl-6-(tert-butyldimethylsilyloxy)-3-methyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-amine

: 1448722-47-1
(1S,3R,4aS,8S,9aR)-11-((benzyloxy)carbonyl)-3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: water; ethanol / 48 h / 20 °C

2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 22 h / 20 °C / Inert atmosphere

3.1: potassium carbonate / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

4.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 5.08 h / -78 °C / Inert atmosphere

5.1: rhodium(II) acetate dimer / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere

6.2: 24.5 h / 0 - 20 °C / Inert atmosphere

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / tetrahydrofuran / 15 h / 20 - 50 °C / Inert atmosphere

8.1: sodium hydroxide; ethanol / 13.5 h / 60 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; rhodium(II) acetate dimer; ethanol; 10 wt% Pd(OH)2 on carbon; hydrogen; sodium hydride; potassium carbonate; lithium chloride; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; mineral oil; 7.1: |Stille Cross Coupling;
DOI:10.1021/ol401954f

Reference yield:

: 1448722-39-1
C₂₄H₃₁NO₅

: 1448722-47-1
(1S,3R,4aS,8S,9aR)-11-((benzyloxy)carbonyl)-3-methyl-7-vinyl-2,3,4,4a,5,8,9,9a-octahydro-1H-1,8-(epiminomethano)benzo[7]annulene-6-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere

1.2: 24.5 h / 0 - 20 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / tetrahydrofuran / 15 h / 20 - 50 °C / Inert atmosphere

3.1: sodium hydroxide; ethanol / 13.5 h / 60 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; ethanol; sodium hydride; lithium chloride; sodium hydroxide; In tetrahydrofuran; mineral oil; 2.1: |Stille Cross Coupling;
DOI:10.1021/ol401954f