ethyl (1R,3S,4S)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate

Base Information

Chemical Name:ethyl (1R,3S,4S)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate
CAS No.:475299-67-3
Molecular Formula:C₁₈H₂₃NO₂
Molecular Weight:285.386
Hs Code.:

Synonyms:ethyl (1R,3S,4S)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate

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Chemical Property of ethyl (1R,3S,4S)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate

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Technology Process of ethyl (1R,3S,4S)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate

There total 1 articles about ethyl (1R,3S,4S)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.2]oct-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: 65.0%

: 1165952-91-9
cyclohexa-1,3-diene

: 851389-20-3
<(R)-(1-phenylethyl)imino>acetic acid ethyl ester

: 134984-64-8
exo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.2>bicyclooct-5-ene

: 475299-67-3
ethyl (1R,3S,4S)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate

Guidance literature:: cyclohexa-1,3-diene; <(R)-(1-phenylethyl)imino>acetic acid ethyl ester; With boron trifluoride diethyl etherate; In dichloromethane; trifluoroacetic acid; at -80 ℃; for 2h;

at 20 ℃; for 72h;
DOI:10.1016/S0040-4039(02)01267-4

Reference yield:

: 475299-67-3
ethyl (1R,3S,4S)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate

: (1R,3S,4R,5R,6S)-5,6-Dihydroxy-2-((R)-1-phenyl-ethyl)-2-aza-bicyclo[2.2.2]octane-3-carboxylic acid ethyl ester

Guidance literature:: With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 20 ℃; for 12h;
DOI:10.1002/ejoc.200300700

Reference yield:

: 475299-67-3
ethyl (1R,3S,4S)-2-[(1R)-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate

: ethyl (1R,3S,4R,5R,6S)-2-[(2S)-2-benzyloxycarbonylamino-3-methoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: K₃Fe(CN)6; K₂CO₃; K₂OsO₂(OH)4 / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

2: 3.40 g / H₂ / Pd/C / ethanol / 24 h / 20 °C / 760 Torr

3: 33 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

With potassium dioxotetrahydroxoosmate(VI); hydrogen; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; potassium hexacyanoferrate(III); palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/ejoc.200300700