(1RS,2SR,4RS,5RS,6SR)-3-benzoyl-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.0^2,4>oct-endo-6-yl acetate

Base Information

• Chemical Name: (1RS,2SR,4RS,5RS,6SR)-3-benzoyl-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.0^2,4>oct-endo-6-yl acetate
• CAS No.: 138748-46-6
• Molecular Formula: C₁₆H₁₄N₂O₄
• Molecular Weight: 298.298

Synonyms:(1RS,2SR,4RS,5RS,6SR)-3-benzoyl-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.0^2,4>oct-endo-6-yl acetate

Chemical Property of (1RS,2SR,4RS,5RS,6SR)-3-benzoyl-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.0^2,4>oct-endo-6-yl acetate

Chemical Property:

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Technology Process of (1RS,2SR,4RS,5RS,6SR)-3-benzoyl-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.0^2,4>oct-endo-6-yl acetate

There total 3 articles about (1RS,2SR,4RS,5RS,6SR)-3-benzoyl-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.0^2,4>oct-endo-6-yl acetate 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: 85.0%

benzoyl chloride (98-88-4) + 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,2SR,4RS,5RS,6SR)-3-benzoyl-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.02,4>oct-endo-6-yl acetate (138748-46-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 24h;

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,2SR,4RS,5RS,6SR)-3-benzoyl-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.02,4>oct-endo-6-yl acetate (138748-46-6)

Guidance literature:

Multi-step reaction with 3 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

With triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1055/s-1991-26607

Reference yield:

tert-butyl (1RS,2SR,4RS,5RS,6SR)-endo-6-acetoxy-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.02,4>octane-3-carboxylate (138748-44-4) → (1RS,2SR,4RS,5RS,6SR)-3-benzoyl-exo-6-cyano-8-oxa-3-azatricyclo<3.2.1.02,4>oct-endo-6-yl acetate (138748-46-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / CF₃COOH / CH₂Cl₂ / 15 h / 20 °C

2: 85 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

With triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1055/s-1991-26607

upstream raw materials:

benzoyl chloride

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

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

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

Downstream raw materials:

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

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

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

(1RS,2SR,3RS,4RS)-exo-3-benzamido-6-oxo-7-oxabicyclo<2.2.1>hept-endo-2-yl acetate

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