(1RS,3RS,5SR,7SR)-8-[(4-methylphenyl)sulfonylyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octane

Base Information

• Chemical Name: (1RS,3RS,5SR,7SR)-8-[(4-methylphenyl)sulfonylyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octane
• CAS No.: 220555-55-5
• Molecular Formula: C₁₃H₁₅NO₃S
• Molecular Weight: 265.333

Synonyms:(1RS,3RS,5SR,7SR)-8-[(4-methylphenyl)sulfonylyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octane

Chemical Property of (1RS,3RS,5SR,7SR)-8-[(4-methylphenyl)sulfonylyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octane

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Technology Process of (1RS,3RS,5SR,7SR)-8-[(4-methylphenyl)sulfonylyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octane

There total 11 articles about (1RS,3RS,5SR,7SR)-8-[(4-methylphenyl)sulfonylyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octane 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: 64.0%

chloroamine-T (127-65-1) + cis-1,2-epoxy-4-cyclohexene (6253-27-6) → (1RS,3RS,5SR,7SR)-8-[(4-methylphenyl)sulfonylyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octane (220555-55-5)

Guidance literature:

With phenyltrimethylammonium tribromide; In acetonitrile; at 28 ℃; for 12h;

DOI:10.1021/jo052357x

Reference yield: 55.0%

7-[(4-methylphenyl)sulfonyl]-7-azabicyclo[4.1.0]hept-3-ene (112297-29-7) → (1RS,3SR,5RS,7SR)-8-[(4-methylphenyl)sulfonylyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octane (220555-54-4) + (1RS,3RS,5SR,7SR)-8-[(4-methylphenyl)sulfonylyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octane (220555-55-5)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 16h; Further Variations:; Reagents; Solvents; Temperatures; time; Product distribution;

DOI:10.1039/b210608f

Reference yield:

cyclohexa-1,4-diene (1165952-92-0) → (1RS,3RS,5SR,7SR)-8-[(4-methylphenyl)sulfonylyl]-4-oxa-8-azatricyclo[5.1.0.03,5]octane (220555-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1: phenyltrimethylammonium tribromide / acetonitrile / 12 h / 28 °C

2: m-chloroperoxybenzoic acid

With phenyltrimethylammonium tribromide; 3-chloro-benzenecarboperoxoic acid; In acetonitrile; 1: Sharpless aziridination;

DOI:10.1021/jo0624389

upstream raw materials:

7-(4-Methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-3-en

p-toluenesulfonyl chloride

(1S,3S,5R,7R)-4-Oxa-8-aza-tricyclo[5.1.0.0^3,5]octane

7-[(4-methylphenyl)sulfonyl]-7-azabicyclo[4.1.0]hept-3-ene

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