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

Base Information

Chemical Name:(-)-8-phenylmenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate
CAS No.:1433821-86-3
Molecular Formula:C₂₃H₃₁NO₃
Molecular Weight:369.504
Hs Code.:

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

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

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

There total 4 articles about (-)-8-phenylmenthyl (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:

: 864062-55-5
(-)-8-phenylmenthyl glyoxylate oxime

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

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

: 1433821-86-3
(-)-8-phenylmenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

: 1433821-92-1
(-)-8-phenylmenthyl (1R,4R,5R)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

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

Reference yield:

: 65253-04-5
(-)-8-phenylmenthol

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

: 1433821-86-3
(-)-8-phenylmenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

: 1433821-92-1
(-)-8-phenylmenthyl (1R,4R,5R)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: dmap; triethylamine / dichloromethane / 3 h / Inert atmosphere; Cooling with ice

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

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

4: trifluoroacetic acid / dichloromethane / 5 h / -20 °C / Inert atmosphere

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

Reference yield:

: 72526-00-2
(-)-8-phenylmenthyl acrylate

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

: 1433821-86-3
(-)-8-phenylmenthyl (1S,4S,5S)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate

: 1433821-92-1
(-)-8-phenylmenthyl (1R,4R,5R)-(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: trifluoroacetic acid / dichloromethane / 5 h / -20 °C / Inert atmosphere

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