(1S,2S,3R,7R)-9-Methyl-3-phenoxy-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one

Base Information

• Chemical Name: (1S,2S,3R,7R)-9-Methyl-3-phenoxy-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one
• CAS No.: 246031-50-5
• Molecular Formula: C₁₄H₁₆N₂O₃
• Molecular Weight: 260.293

Synonyms:(1S,2S,3R,7R)-9-Methyl-3-phenoxy-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one

Chemical Property of (1S,2S,3R,7R)-9-Methyl-3-phenoxy-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one

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Technology Process of (1S,2S,3R,7R)-9-Methyl-3-phenoxy-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-one

There total 2 articles about (1S,2S,3R,7R)-9-Methyl-3-phenoxy-8-oxa-5,9-diaza-tricyclo[5.2.1.0^2,5]decan-4-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: 80.0%

N-methylhydroxyamine hydrochloride (4229-44-1) + (+)-(3R,4S)-4-formyl-3-phenoxy-1-(2-propenyl)-2-azetidinone (201748-24-5) → (1S,2S,3R,7R)-9-Methyl-3-phenoxy-8-oxa-5,9-diaza-tricyclo[5.2.1.02,5]decan-4-one (246031-50-5)

Guidance literature:

With triethylamine; In benzene; Heating;

DOI:10.1016/S0040-4039(99)01013-8

Reference yield:

(3R,4S)-1-Allyl-4-hydroxymethyl-3-phenoxy-azetidin-2-one → (1S,2S,3R,7R)-9-Methyl-3-phenoxy-8-oxa-5,9-diaza-tricyclo[5.2.1.02,5]decan-4-one (246031-50-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: PTSA / tetrahydrofuran; H₂O / Heating

1.2: 98 percent / NaIO₄; NaHCO₃ / CH₂Cl₂ / 20 °C

2.1: 80 percent / Et₃N / benzene / Heating

With toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; water; benzene; 1.1: Hydrolysis / 1.2: Oxidation / 2.1: Cycloaddition;

DOI:10.1016/S0040-4039(99)01013-8

Reference yield: 80.0%

(1S,2S,3R,7R)-9-Methyl-3-phenoxy-8-oxa-5,9-diaza-tricyclo[5.2.1.02,5]decan-4-one (246031-50-5) → (3R,5S,6S,7R)-3-Hydroxy-5-methylamino-7-phenoxy-1-aza-bicyclo[4.2.0]octan-8-one (246031-62-9)

Guidance literature:

With zinc; In water; acetic acid; for 24h; Heating;

DOI:10.1016/S0040-4039(99)01013-8

upstream raw materials:

N-methylhydroxyamine hydrochloride

(+)-(3R,4S)-4-formyl-3-phenoxy-1-(2-propenyl)-2-azetidinone

Downstream raw materials:

(3R,5S,6S,7R)-3-Hydroxy-5-methylamino-7-phenoxy-1-aza-bicyclo[4.2.0]octan-8-one

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