(3aR,5R,6S)-5-(1,3-dioxolan-2-yl)-6-(4-fluorophenyl)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole

Base Information

• Chemical Name: (3aR,5R,6S)-5-(1,3-dioxolan-2-yl)-6-(4-fluorophenyl)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole
• CAS No.: 1087041-41-5
• Molecular Formula: C₁₅H₁₆FNO₃
• Molecular Weight: 277.295

Synonyms:(3aR,5R,6S)-5-(1,3-dioxolan-2-yl)-6-(4-fluorophenyl)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole

Chemical Property of (3aR,5R,6S)-5-(1,3-dioxolan-2-yl)-6-(4-fluorophenyl)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole

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Technology Process of (3aR,5R,6S)-5-(1,3-dioxolan-2-yl)-6-(4-fluorophenyl)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole

There total 1 articles about (3aR,5R,6S)-5-(1,3-dioxolan-2-yl)-6-(4-fluorophenyl)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole 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: 80.0%

2-((R)-1-[(S)-1-(4-fluorophenyl)-2-nitroethyl]-but-3-enyl)-1,3-dioxolane (1087041-21-1) → (3aR,5R,6S)-5-(1,3-dioxolan-2-yl)-6-(4-fluorophenyl)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole (1087041-41-5)

Guidance literature:

2-((R)-1-[(S)-1-(4-fluorophenyl)-2-nitroethyl]-but-3-enyl)-1,3-dioxolane; With chloro-trimethyl-silane; triethylamine; In tetrahydrofuran; at -90 - 0 ℃; for 2h; Inert atmosphere;

With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at 20 ℃; for 15h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 0 ℃; for 1h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol8023133

Reference yield: 63.0%

(3aR,5R,6S)-5-(1,3-dioxolan-2-yl)-6-(4-fluorophenyl)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole (1087041-41-5) → (2S,3R,5S)-3-(1,3-dioxolan-2-yl)-2-(4-fluorophenyl)-5-hydroxymethyl-cyclopentanone (1087041-63-1)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; boric acid; In methanol; water; at 50 ℃; for 18h;

DOI:10.1021/ol8023133

upstream raw materials:

2-((R)-1-[(S)-1-(4-fluorophenyl)-2-nitroethyl]-but-3-enyl)-1,3-dioxolane

Downstream raw materials:

(2S,3R,5S)-3-(1,3-dioxolan-2-yl)-2-(4-fluorophenyl)-5-hydroxymethyl-cyclopentanone

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