(1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1R,8S,11S)-1-methyl-11-phenyl-9-aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl)-ethyl]-cyclohexanol

Base Information

• Chemical Name: (1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1R,8S,11S)-1-methyl-11-phenyl-9-aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl)-ethyl]-cyclohexanol
• CAS No.: 334706-77-3
• Molecular Formula: C₂₇H₃₅NO
• Molecular Weight: 389.581

Synonyms:(1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1R,8S,11S)-1-methyl-11-phenyl-9-aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl)-ethyl]-cyclohexanol

Chemical Property of (1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1R,8S,11S)-1-methyl-11-phenyl-9-aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl)-ethyl]-cyclohexanol

Chemical Property:

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Technology Process of (1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1R,8S,11S)-1-methyl-11-phenyl-9-aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl)-ethyl]-cyclohexanol

There total 6 articles about (1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1R,8S,11S)-1-methyl-11-phenyl-9-aza-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-trien-9-yl)-ethyl]-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: 73.0%

(2S,7R,9R,10S)-2-(o-bromophenyl)-3-(2'-methyl)cinnamyl-4,4,7-trimethyl-octahydro-2H-1,3-benzoxazine → (1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1S,8R,11R)-1-methyl-11-phenyl-9-aza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-trien-9-yl)-ethyl]-cyclohexanol + (1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1R,8S,11S)-1-methyl-11-phenyl-9-aza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-trien-9-yl)-ethyl]-cyclohexanol (334706-77-3)

Guidance literature:

With tert.-butyl lithium; In diethyl ether; at -90 - 20 ℃; for 2h;

DOI:10.1021/ja002864q

Reference yield:

(-)-aminomenthol (55179-51-6) → (1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1R,8S,11S)-1-methyl-11-phenyl-9-aza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-trien-9-yl)-ethyl]-cyclohexanol (334706-77-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / CH₂Cl₂ / 20 °C

2: 90 percent / NaBH₄ / ethanol / 20 °C

3: 82 percent / 120 °C

4: 73 percent / t-BuLi / diethyl ether / 2 h / -90 - 20 °C

With sodium tetrahydroborate; tert.-butyl lithium; In diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ja002864q

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → (1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1R,8S,11S)-1-methyl-11-phenyl-9-aza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-trien-9-yl)-ethyl]-cyclohexanol (334706-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 120 °C

2: 73 percent / t-BuLi / diethyl ether / 2 h / -90 - 20 °C

With tert.-butyl lithium; In diethyl ether;

DOI:10.1021/ja002864q

upstream raw materials:

(-)-aminomenthol

ortho-bromobenzaldehyde

α-methyl-trans-cinnamaldehyde

(2S,7R,9R,10S)-2-[(1'-methyl-2'-phenyl)vinyl]-4,4,7-trimethyl-octahydro-2H-1,3-benzoxazine

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