(t)-8-phenylneomenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

Base Information

Chemical Name:(t)-8-phenylneomenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate
CAS No.:1433822-02-6
Molecular Formula:C₂₃H₃₁NO₃
Molecular Weight:369.504
Hs Code.:

Synonyms:(t)-8-phenylneomenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

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Chemical Property of (t)-8-phenylneomenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

Chemical Property:

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Technology Process of (t)-8-phenylneomenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

There total 7 articles about (t)-8-phenylneomenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate 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:

: 1433821-67-0
(+)-8-phenylneomenthyl glyoxylate oxime

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: (+)-8-phenylneomenthyl (1S,4R)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene-3-endo-carboxylate

: 1433821-97-6
(+)-8-phenylneomenthyl (1R,4R,5R)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

: 1433822-02-6
(t)-8-phenylneomenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

Guidance literature:: With boron trifluoride; In dichloromethane; at -20 ℃; for 5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2013.03.033

Reference yield:

: 1433821-67-0
(+)-8-phenylneomenthyl glyoxylate oxime

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: (+)-8-phenylneomenthyl (1R,4S)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene-3-exo-carboxylate

: (+)-8-phenylneomenthyl (1S,4R)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene-3-exo-carboxylate

: (+)-8-phenylneomenthyl (1S,4R)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene-3-endo-carboxylate

: 1433821-97-6
(+)-8-phenylneomenthyl (1R,4R,5R)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

: 1433822-02-6
(t)-8-phenylneomenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at -20 ℃; for 5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2013.03.033

Reference yield:

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

: (+)-8-phenylneomenthyl (1S,4R)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene-3-endo-carboxylate

: 1433821-97-6
(+)-8-phenylneomenthyl (1R,4R,5R)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

: 1433822-02-6
(t)-8-phenylneomenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: osmium(VIII) oxide / 1,4-dioxane; water / 0.08 h

2: dmap; triethylamine; hydroxylamine hydrochloride / dichloromethane / 20 °C / Inert atmosphere

3: boron trifluoride / dichloromethane / 5 h / -20 °C / Inert atmosphere

With dmap; osmium(VIII) oxide; boron trifluoride; hydroxylamine hydrochloride; triethylamine; In 1,4-dioxane; dichloromethane; water;
DOI:10.1016/j.tet.2013.03.033