(1R,2S,6R,7S)-1,10,10-Trimethyl-4-phenethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 5-oxide

Base Information

• Chemical Name: (1R,2S,6R,7S)-1,10,10-Trimethyl-4-phenethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 5-oxide
• CAS No.: 206438-90-6
• Molecular Formula: C₁₉H₂₅NO₂
• Molecular Weight: 299.413

Synonyms:(1R,2S,6R,7S)-1,10,10-Trimethyl-4-phenethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 5-oxide

Chemical Property of (1R,2S,6R,7S)-1,10,10-Trimethyl-4-phenethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 5-oxide

Chemical Property:

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Technology Process of (1R,2S,6R,7S)-1,10,10-Trimethyl-4-phenethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 5-oxide

There total 1 articles about (1R,2S,6R,7S)-1,10,10-Trimethyl-4-phenethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 5-oxide 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:

trimethyl 3-phenylorthopropionate (54917-78-1) + (+)-3-(hydroxylamino)isoborneol hydrochloride → (1R,2S,6R,7S)-1,10,10-Trimethyl-4-phenethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-ene 5-oxide (206438-90-6)

Guidance literature:

With calcium carbonate; In toluene; at 40 ℃; for 3h;

DOI:10.1016/S0040-4039(98)00062-8

Reference yield:

(1R,2S,6R,7S)-1,10,10-Trimethyl-4-phenethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-ene 5-oxide (206438-90-6) → D-phenyllactic acid (828-01-3,7326-19-4,20312-36-1,156-05-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, 4-dimethylamino pyridine / -20 deg C, 1 h, 20 deg C, 16 h

2: 71 percent / NaHCO₃ / CH₂Cl₂; H₂O / 16 h / 20 °C

3: NaOH / methanol / 16 h / 80 °C

With dmap; sodium hydroxide; sodium hydrogencarbonate; triethylamine; In methanol; dichloromethane; water;

DOI:10.1016/S0040-4039(98)00062-8

Reference yield:

(1R,2S,6R,7S)-1,10,10-Trimethyl-4-phenethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-ene 5-oxide (206438-90-6) → methyl 2-hydroxy-3-phenylpropionate (27000-00-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N, 4-dimethylamino pyridine / -20 deg C, 1 h, 20 deg C, 16 h

2: 71 percent / NaHCO₃ / CH₂Cl₂; H₂O / 16 h / 20 °C

3: NaOH / methanol / 16 h / 80 °C

4: diethyl ether / 0.08 h / 0 °C

With dmap; sodium hydroxide; sodium hydrogencarbonate; triethylamine; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4039(98)00062-8

upstream raw materials:

trimethyl 3-phenylorthopropionate

Downstream raw materials:

Acetic acid (R)-2-phenyl-1-((1R,2S,6R,7S)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-ethyl ester

D-phenyllactic acid

methyl 2-hydroxy-3-phenylpropionate

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