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

Base Information

Chemical Name:(-)-(1R,2S,5R)-8-phenylmenthyl (1S,3S,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
CAS No.:161607-17-6
Molecular Formula:C₃₁H₃₉NO₂
Molecular Weight:457.656
Hs Code.:

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

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Chemical Property of (-)-(1R,2S,5R)-8-phenylmenthyl (1S,3S,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

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Technology Process of (-)-(1R,2S,5R)-8-phenylmenthyl (1S,3S,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

There total 3 articles about (-)-(1R,2S,5R)-8-phenylmenthyl (1S,3S,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-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:

: BF₃*C₂HF₃O₂*C₂₆H₃₃NO₂

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

: 1333161-36-6
(-)-(1R,2S,5R)-8-phenylmenthyl (1R,3S,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

: 161607-17-6
(-)-(1R,2S,5R)-8-phenylmenthyl (1S,3S,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

: 1333161-35-5
(+)-(1R,2S,5R)-8-phenylmenthyl (1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Guidance literature:: BF₃*C₂HF₃O₂*C₂₆H₃₃NO₂; cyclopenta-1,3-diene; In dichloromethane; at -78 ℃; for 5h; Inert atmosphere;

With sodium hydrogencarbonate; In dichloromethane; water; diastereoselective reaction;
DOI:10.1016/j.tet.2011.06.097

Reference yield:

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

: 161607-17-6
(-)-(1R,2S,5R)-8-phenylmenthyl (1S,3S,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

: 1333161-35-5
(+)-(1R,2S,5R)-8-phenylmenthyl (1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: ozone / methanol; dichloromethane / 0.33 h / -78 °C

2.2: 12 h / Inert atmosphere

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

With dmap; ozone; triethylamine; In methanol; dichloromethane; 3.1: aza-Diels-Alder reaction;
DOI:10.1016/j.tet.2011.06.097

Reference yield:

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

: 161607-17-6
(-)-(1R,2S,5R)-8-phenylmenthyl (1S,3S,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

: 1333161-35-5
(+)-(1R,2S,5R)-8-phenylmenthyl (1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: ozone / methanol; dichloromethane / 0.33 h / -78 °C

1.2: 12 h / Inert atmosphere

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

With ozone; In methanol; dichloromethane; 2.1: aza-Diels-Alder reaction;
DOI:10.1016/j.tet.2011.06.097