Naphthalene-2-carboxylic acid (1R,2R,6S,7S,10R)-10-ethyl-4-(4-methoxy-benzyl)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-10-yl ester

Base Information

• Chemical Name: Naphthalene-2-carboxylic acid (1R,2R,6S,7S,10R)-10-ethyl-4-(4-methoxy-benzyl)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-10-yl ester
• CAS No.: 182677-60-7
• Molecular Formula: C₃₀H₂₉NO₅
• Molecular Weight: 483.564

Synonyms:Naphthalene-2-carboxylic acid (1R,2R,6S,7S,10R)-10-ethyl-4-(4-methoxy-benzyl)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-10-yl ester

Chemical Property of Naphthalene-2-carboxylic acid (1R,2R,6S,7S,10R)-10-ethyl-4-(4-methoxy-benzyl)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-10-yl ester

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Technology Process of Naphthalene-2-carboxylic acid (1R,2R,6S,7S,10R)-10-ethyl-4-(4-methoxy-benzyl)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-10-yl ester

There total 5 articles about Naphthalene-2-carboxylic acid (1R,2R,6S,7S,10R)-10-ethyl-4-(4-methoxy-benzyl)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-10-yl ester 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: 81.0%

(1R,2R,6S,7S,10R)-10-Ethyl-10-hydroxy-4-(4-methoxy-benzyl)-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione (182677-59-4) + 2-naphthaloyl chloride (2243-83-6) → Naphthalene-2-carboxylic acid (1R,2R,6S,7S,10R)-10-ethyl-4-(4-methoxy-benzyl)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-10-yl ester (182677-60-7)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/0040-4039(96)01303-2

Reference yield:

(3aR,4R,7S,7aS)-hexahydro-8-isopropylidene-4,7-methano-1H-isoindole-1,3(2H)-dione (166878-52-0) → Naphthalene-2-carboxylic acid (1R,2R,6S,7S,10R)-10-ethyl-4-(4-methoxy-benzyl)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-10-yl ester (182677-60-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / KHMDS

2: 1) O₃ / 1) CH₂Cl₂, -78 deg C, 2) THF, -78 deg C

3: 100 percent / hydrogen / Pd/C

4: 81 percent / KHMDS / tetrahydrofuran / 0 °C

With hydrogen; potassium hexamethylsilazane; ozone; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)01303-2

Reference yield:

(3aR,4R,7S,7aS)-8-(propan-2-ylidene)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (217649-81-5) → Naphthalene-2-carboxylic acid (1R,2R,6S,7S,10R)-10-ethyl-4-(4-methoxy-benzyl)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-10-yl ester (182677-60-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / hydrogen / Pd/C

2: 75 percent / KHMDS

3: 1) O₃ / 1) CH₂Cl₂, -78 deg C, 2) THF, -78 deg C

4: 100 percent / hydrogen / Pd/C

5: 81 percent / KHMDS / tetrahydrofuran / 0 °C

With hydrogen; potassium hexamethylsilazane; ozone; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)01303-2

upstream raw materials:

(1R,2R,6S,7S,10R)-10-Ethyl-10-hydroxy-4-(4-methoxy-benzyl)-4-aza-tricyclo[5.2.1.0^2,6]decane-3,5-dione

2-naphthaloyl chloride

(3aR,4R,7S,7aS)-hexahydro-8-isopropylidene-4,7-methano-1H-isoindole-1,3(2H)-dione

(3aR,4R,7S,7aS)-8-(propan-2-ylidene)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

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