acetic acid 5,6-dihydroxy-2-(1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-3-ylmethyl ester

Base Information

Chemical Name:acetic acid 5,6-dihydroxy-2-(1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-3-ylmethyl ester
CAS No.:915306-70-6
Molecular Formula:C₁₇H₂₃NO₄
Molecular Weight:305.374
Hs Code.:

Synonyms:acetic acid 5,6-dihydroxy-2-(1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-3-ylmethyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of acetic acid 5,6-dihydroxy-2-(1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-3-ylmethyl ester

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Technology Process of acetic acid 5,6-dihydroxy-2-(1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-3-ylmethyl ester

There total 5 articles about acetic acid 5,6-dihydroxy-2-(1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-3-ylmethyl 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: 80.0%

: acetic acid 2-(1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-5-en-3-ylmethyl ester

: 915306-70-6
acetic acid 5,6-dihydroxy-2-(1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-3-ylmethyl ester

Guidance literature:: With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; water; at 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2006.08.077

Reference yield:

: 915306-61-5
(-)-(1S,3S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-en-3-ylmethanol

: 915306-70-6
acetic acid 5,6-dihydroxy-2-(1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

2: 80 percent / N-methylmorpholine N-oxide / OsO₄ / dioxane; tetrahydrofuran; H₂O / 12 h / 20 °C

With dmap; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;
DOI:10.1016/j.tetlet.2006.08.077

Reference yield:

: 3886-69-9
(R)-1-phenyl-ethyl-amine

: 915306-70-6
acetic acid 5,6-dihydroxy-2-(1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: TFA; BF₃*OEt₂ / CH₂Cl₂ / -78 °C

2: 96 percent / LiAlH₄ / diethyl ether / 5 h / 20 °C

3: 89 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

4: 80 percent / N-methylmorpholine N-oxide / OsO₄ / dioxane; tetrahydrofuran; H₂O / 12 h / 20 °C

With dmap; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; 1: aza-Diels-Alder reaction;
DOI:10.1016/j.tetlet.2006.08.077