(1R,2S,5R)-2-((1R,8S)-1-9-Aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl-1-methyl-ethyl)-5-methyl-cyclohexanol

Base Information

• Chemical Name: (1R,2S,5R)-2-((1R,8S)-1-9-Aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl-1-methyl-ethyl)-5-methyl-cyclohexanol
• CAS No.: 334706-72-8
• Molecular Formula: C₂₀H₂₉NO
• Molecular Weight: 299.456

Synonyms:(1R,2S,5R)-2-((1R,8S)-1-9-Aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl-1-methyl-ethyl)-5-methyl-cyclohexanol

Chemical Property of (1R,2S,5R)-2-((1R,8S)-1-9-Aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl-1-methyl-ethyl)-5-methyl-cyclohexanol

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Technology Process of (1R,2S,5R)-2-((1R,8S)-1-9-Aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl-1-methyl-ethyl)-5-methyl-cyclohexanol

There total 4 articles about (1R,2S,5R)-2-((1R,8S)-1-9-Aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl-1-methyl-ethyl)-5-methyl-cyclohexanol 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%

N-allyl-2α-(o-bromophenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine (203190-42-5) → (2S,4aS,7R,8aR)-3-Allyl-4,4,7-trimethyl-2-phenyl-octahydro-benzo[e][1,3]oxazine + (5S,7aS,10R,11aR,12aS)-5,7,7,10-Tetramethyl-5,7a,8,9,10,11,11a,12a-octahydro-6H,7H-12-oxa-6a-aza-benzo[a]anthracene + (1R,2S,5R)-2-((1R,8S)-1-9-Aza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-trien-9-yl-1-methyl-ethyl)-5-methyl-cyclohexanol (334706-72-8)

Guidance literature:

N-allyl-2α-(o-bromophenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine; With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; In diethyl ether; at -90 ℃;

In diethyl ether; pentane; at -90 - 20 ℃; for 8h; Further stages.;

DOI:10.1021/ja002864q

Reference yield:

(-)-aminomenthol (55179-51-6) → (1R,2S,5R)-2-((1R,8S)-1-9-Aza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-trien-9-yl-1-methyl-ethyl)-5-methyl-cyclohexanol (334706-72-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / CH₂Cl₂ / 20 °C

2.1: 89 percent / K₂CO₃ / acetonitrile / Heating

3.1: t-BuLi; TMEDA / diethyl ether / -90 °C

3.2: 80 percent / diethyl ether; pentane / 8 h / -90 - 20 °C

With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; potassium carbonate; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ja002864q

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → (1R,2S,5R)-2-((1R,8S)-1-9-Aza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-trien-9-yl-1-methyl-ethyl)-5-methyl-cyclohexanol (334706-72-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / CH₂Cl₂ / 20 °C

2.1: 89 percent / K₂CO₃ / acetonitrile / Heating

3.1: t-BuLi; TMEDA / diethyl ether / -90 °C

3.2: 80 percent / diethyl ether; pentane / 8 h / -90 - 20 °C

With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; potassium carbonate; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ja002864q

upstream raw materials:

N-allyl-2α-(o-bromophenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine

(-)-aminomenthol

ortho-bromobenzaldehyde

2α-(o-bromophenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine

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