(1RS,2RS,6RS,7RS)-9,9-dimethoxy-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-ene

Base Information

• Chemical Name: (1RS,2RS,6RS,7RS)-9,9-dimethoxy-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-ene
• CAS No.: 138748-59-1
• Molecular Formula: C₁₅H₁₇NO₄
• Molecular Weight: 275.304

Synonyms:(1RS,2RS,6RS,7RS)-9,9-dimethoxy-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-ene

Chemical Property of (1RS,2RS,6RS,7RS)-9,9-dimethoxy-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-ene

Chemical Property:

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Technology Process of (1RS,2RS,6RS,7RS)-9,9-dimethoxy-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-ene

There total 6 articles about (1RS,2RS,6RS,7RS)-9,9-dimethoxy-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-ene 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: 92.0%

methanol (67-56-1) + (1RS,2RS,6RS,7RS)-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.02,6>dec-4-en-9-one (138748-52-4) → (1RS,2RS,6RS,7RS)-9,9-dimethoxy-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.02,6>dec-4-ene (138748-59-1)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 2h;

DOI:10.1055/s-1991-26607

Reference yield:

2-endo-acetoxy-7-oxabicyclo<2.2.1>hept-5-ene-2-exo-carbonitrile (79902-01-5,84120-97-8,84120-98-9,84424-28-2,94482-74-3,105497-65-2,120056-66-8,148346-15-0) → (1RS,2RS,6RS,7RS)-9,9-dimethoxy-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.02,6>dec-4-ene (138748-59-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) acetone, 50 deg C, 2 d, 2.) acetone, 0 deg C, irradiation, 5 h

2: 98 percent / CF₃COOH / CH₂Cl₂ / 15 h / 20 °C

3: 85 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

4: 12 percent / 70percent aq. HClO₄, 1,1,1,3,3,3-hexafluoro-2-propanol / 24 h / 20 °C

5: 71 percent / K₂CO₃, 37percent aq. formaldehyde / methanol / 2.5 h / 20 °C

6: 92 percent / gaseous HCl / 2 h / 20 °C

With hydrogenchloride; formaldehyd; perchloric acid; 1,1,1,3',3',3'-hexafluoro-propanol; potassium carbonate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1055/s-1991-26607

Reference yield:

Acetic acid (1S,2R,4S,5S,6R)-6-cyano-8-oxa-3-aza-tricyclo[3.2.1.02,4]oct-6-yl ester (138748-45-5) → (1RS,2RS,6RS,7RS)-9,9-dimethoxy-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.02,6>dec-4-ene (138748-59-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

2: 12 percent / 70percent aq. HClO₄, 1,1,1,3,3,3-hexafluoro-2-propanol / 24 h / 20 °C

3: 71 percent / K₂CO₃, 37percent aq. formaldehyde / methanol / 2.5 h / 20 °C

4: 92 percent / gaseous HCl / 2 h / 20 °C

With hydrogenchloride; formaldehyd; perchloric acid; 1,1,1,3',3',3'-hexafluoro-propanol; potassium carbonate; triethylamine; In methanol; dichloromethane;

DOI:10.1055/s-1991-26607

upstream raw materials:

methanol

(1RS,2RS,6RS,7RS)-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-en-9-one

2-endo-acetoxy-7-oxabicyclo<2.2.1>hept-5-ene-2-exo-carbonitrile

Acetic acid (1S,2R,4S,5S,6R)-6-cyano-8-oxa-3-aza-tricyclo[3.2.1.0^2,4]oct-6-yl ester

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