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

Base Information

• Chemical Name: (1RS,2RS,6RS,7RS)-4-(phenylamino)-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-en-9-one
• CAS No.: 138748-53-5
• Molecular Formula: C₁₃H₁₂N₂O₃
• Molecular Weight: 244.25

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

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

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

There total 5 articles about (1RS,2RS,6RS,7RS)-4-(phenylamino)-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-en-9-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: 48.0%

(1RS,2RS,6RS,7RS,9SR)-exo-9-cyano-4-phenylamino-3,10-dioxa-5-azatricyclo<5.2.1.02,6>dec-4-en-endo-9-yl acetate (138748-50-2) → (1RS,2RS,6RS,7RS)-4-(phenylamino)-3,10-dioxa-5-azatricyclo<5.2.1.02,6>dec-4-en-9-one (138748-53-5)

Guidance literature:

With formaldehyd; sodium methylate; In methanol; at 20 ℃; for 6h;

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)-4-(phenylamino)-3,10-dioxa-5-azatricyclo<5.2.1.02,6>dec-4-en-9-one (138748-53-5)

Guidance literature:

Multi-step reaction with 5 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: 78 percent / CH₂Cl₂ / 4 °C

4: 74 percent / trifluoromethanesulfonic anhydride, trifluoromethanesulfonic acid, 1,1,1,3,3,3-hexafluoro-2-propanol / 24 h / 20 °C

5: 48 percent / 30percent NaOMe, 37percent aq. formaldehyde / methanol / 6 h / 20 °C

With formaldehyd; trifluorormethanesulfonic acid; 1,1,1,3',3',3'-hexafluoro-propanol; sodium methylate; trifluoromethanesulfonic acid anhydride; 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)-4-(phenylamino)-3,10-dioxa-5-azatricyclo<5.2.1.02,6>dec-4-en-9-one (138748-53-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / CH₂Cl₂ / 4 °C

2: 74 percent / trifluoromethanesulfonic anhydride, trifluoromethanesulfonic acid, 1,1,1,3,3,3-hexafluoro-2-propanol / 24 h / 20 °C

3: 48 percent / 30percent NaOMe, 37percent aq. formaldehyde / methanol / 6 h / 20 °C

With formaldehyd; trifluorormethanesulfonic acid; 1,1,1,3',3',3'-hexafluoro-propanol; sodium methylate; trifluoromethanesulfonic acid anhydride; In methanol; dichloromethane;

DOI:10.1055/s-1991-26607

upstream raw materials:

(1RS,2RS,6RS,7RS,9SR)-exo-9-cyano-4-phenylamino-3,10-dioxa-5-azatricyclo<5.2.1.0^2,6>dec-4-en-endo-9-yl acetate

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

tert-butyl (1RS,2SR,4RS,5RS,6SR)-endo-6-acetoxy-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.0^2,4>octane-3-carboxylate

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