(2R,7R)-10-Benzoyl-9-oxa-10-aza-tricyclo[6.2.2.0^2,7]dodec-4-ene-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,7R)-10-Benzoyl-9-oxa-10-aza-tricyclo[6.2.2.0^2,7]dodec-4-ene-2-carboxylic acid methyl ester
• CAS No.: 92012-06-1
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38

Synonyms:(2R,7R)-10-Benzoyl-9-oxa-10-aza-tricyclo[6.2.2.0^2,7]dodec-4-ene-2-carboxylic acid methyl ester

Chemical Property of (2R,7R)-10-Benzoyl-9-oxa-10-aza-tricyclo[6.2.2.0^2,7]dodec-4-ene-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2R,7R)-10-Benzoyl-9-oxa-10-aza-tricyclo[6.2.2.0^2,7]dodec-4-ene-2-carboxylic acid methyl ester

There total 4 articles about (2R,7R)-10-Benzoyl-9-oxa-10-aza-tricyclo[6.2.2.0^2,7]dodec-4-ene-2-carboxylic acid methyl ester 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: 70.0%

methyl N-benzoyl-3-aza-2-oxabicyclo<2.2.2>oct-5-ene-5-carboxylate (92011-99-9) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → (2R,7R)-10-Benzoyl-9-oxa-10-aza-tricyclo[6.2.2.02,7]dodec-4-ene-2-carboxylic acid methyl ester (92012-06-1)

Guidance literature:

In 1,3,5-trimethyl-benzene; at 140 ℃; for 48h;

DOI:10.1021/jo00195a057

Reference yield:

3-Benzoyl-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-5-carbaldehyde → (2R,7R)-10-Benzoyl-9-oxa-10-aza-tricyclo[6.2.2.02,7]dodec-4-ene-2-carboxylic acid methyl ester (92012-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / 1,3,5-trimethyl-benzene / 48 h / 140 °C

2: 1) pyridinium dichromate / 1) DMF, 25 deg C, 9h, 2) ether, 0 deg C, 5h

With dipyridinium dichromate; In 1,3,5-trimethyl-benzene;

DOI:10.1021/jo00195a057

Reference yield:

N-benzoyl-3-aza-5-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxabicyclo<2.2.2>oct-5-ene (92011-95-5) → (2R,7R)-10-Benzoyl-9-oxa-10-aza-tricyclo[6.2.2.02,7]dodec-4-ene-2-carboxylic acid methyl ester (92012-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) (n-Bu)4NF, 2) MnO₂ / 1) in THF, 25 deg C, 15 min., 2) in CH₂Cl₂, 25 deg C, 1h

2: 70 percent / 1,3,5-trimethyl-benzene / 48 h / 140 °C

3: 1) pyridinium dichromate / 1) DMF, 25 deg C, 9h, 2) ether, 0 deg C, 5h

With manganese(IV) oxide; dipyridinium dichromate; tetrabutyl ammonium fluoride; In 1,3,5-trimethyl-benzene;

DOI:10.1021/jo00195a057

upstream raw materials:

diazomethane

N-benzoyl 3-aza-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxaldehyde

methyl N-benzoyl-3-aza-2-oxabicyclo<2.2.2>oct-5-ene-5-carboxylate

buta-1,3-diene

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