(+)-(1S,3R,4R)-2-[(1R)-1-phenylethyl]-3-[(1S,2S,5R)-8-phenylneomenthyl-oxycarbonyl]-2-azabicyclo[2.2.1]hept-5-en-2-ammonium trifluoroacetate

Base Information

Chemical Name:(+)-(1S,3R,4R)-2-[(1R)-1-phenylethyl]-3-[(1S,2S,5R)-8-phenylneomenthyl-oxycarbonyl]-2-azabicyclo[2.2.1]hept-5-en-2-ammonium trifluoroacetate
CAS No.:1333161-40-2
Molecular Formula:C₂HF₃O₂*C₃₁H₃₉NO₂
Molecular Weight:571.68
Hs Code.:

Synonyms:(+)-(1S,3R,4R)-2-[(1R)-1-phenylethyl]-3-[(1S,2S,5R)-8-phenylneomenthyl-oxycarbonyl]-2-azabicyclo[2.2.1]hept-5-en-2-ammonium trifluoroacetate

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Chemical Property of (+)-(1S,3R,4R)-2-[(1R)-1-phenylethyl]-3-[(1S,2S,5R)-8-phenylneomenthyl-oxycarbonyl]-2-azabicyclo[2.2.1]hept-5-en-2-ammonium trifluoroacetate

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Technology Process of (+)-(1S,3R,4R)-2-[(1R)-1-phenylethyl]-3-[(1S,2S,5R)-8-phenylneomenthyl-oxycarbonyl]-2-azabicyclo[2.2.1]hept-5-en-2-ammonium trifluoroacetate

There total 4 articles about (+)-(1S,3R,4R)-2-[(1R)-1-phenylethyl]-3-[(1S,2S,5R)-8-phenylneomenthyl-oxycarbonyl]-2-azabicyclo[2.2.1]hept-5-en-2-ammonium trifluoroacetate 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%

: 1333161-39-9
(+)-(1S,2S,5R)-8-phenylmenthyl (1S,3R,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

: 76-05-1
trifluoroacetic acid

: 1333161-40-2
(+)-(1S,3R,4R)-2-[(1R)-1-phenylethyl]-3-[(1S,2S,5R)-8-phenylneomenthyl-oxycarbonyl]-2-azabicyclo[2.2.1]hept-5-en-2-ammonium trifluoroacetate

Guidance literature:: In diethyl ether; at 20 ℃;
DOI:10.1016/j.tet.2011.06.097

Reference yield:

: 104870-75-9
(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexan-1-ol

: 1333161-40-2
(+)-(1S,3R,4R)-2-[(1R)-1-phenylethyl]-3-[(1S,2S,5R)-8-phenylneomenthyl-oxycarbonyl]-2-azabicyclo[2.2.1]hept-5-en-2-ammonium trifluoroacetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2.1: sodium periodate; osmium(VIII) oxide; water / 1,4-dioxane / 2.5 h / 20 °C

2.2: 1 h / 0 °C / Inert atmosphere; Molecular sieve

2.3: -78 °C / Inert atmosphere

3.1: dichloromethane / 5 h / -78 °C / Inert atmosphere

4.1: diethyl ether / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; water; triethylamine; In 1,4-dioxane; diethyl ether; dichloromethane; 3.1: aza-Diels-Alder reaction;
DOI:10.1016/j.tet.2011.06.097

Reference yield:

: 849113-76-4
(+)-(1S,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate

: 1333161-40-2
(+)-(1S,3R,4R)-2-[(1R)-1-phenylethyl]-3-[(1S,2S,5R)-8-phenylneomenthyl-oxycarbonyl]-2-azabicyclo[2.2.1]hept-5-en-2-ammonium trifluoroacetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium periodate; osmium(VIII) oxide; water / 1,4-dioxane / 2.5 h / 20 °C

1.2: 1 h / 0 °C / Inert atmosphere; Molecular sieve

1.3: -78 °C / Inert atmosphere

2.1: dichloromethane / 5 h / -78 °C / Inert atmosphere

3.1: diethyl ether / 20 °C

With sodium periodate; osmium(VIII) oxide; water; In 1,4-dioxane; diethyl ether; dichloromethane; 2.1: aza-Diels-Alder reaction;
DOI:10.1016/j.tet.2011.06.097