(1R,2S,3aR,5R,7aR,8R)-2-(1-Hydroxy-1-methyl-ethyl)-3a,5-dimethyl-8-o-tolyl-octahydro-1,5-methano-inden-6-one

Base Information

• Chemical Name: (1R,2S,3aR,5R,7aR,8R)-2-(1-Hydroxy-1-methyl-ethyl)-3a,5-dimethyl-8-o-tolyl-octahydro-1,5-methano-inden-6-one
• CAS No.: 197306-33-5
• Molecular Formula: C₂₂H₃₀O₂
• Molecular Weight: 326.479

Synonyms:(1R,2S,3aR,5R,7aR,8R)-2-(1-Hydroxy-1-methyl-ethyl)-3a,5-dimethyl-8-o-tolyl-octahydro-1,5-methano-inden-6-one

Chemical Property of (1R,2S,3aR,5R,7aR,8R)-2-(1-Hydroxy-1-methyl-ethyl)-3a,5-dimethyl-8-o-tolyl-octahydro-1,5-methano-inden-6-one

Chemical Property:

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Technology Process of (1R,2S,3aR,5R,7aR,8R)-2-(1-Hydroxy-1-methyl-ethyl)-3a,5-dimethyl-8-o-tolyl-octahydro-1,5-methano-inden-6-one

There total 3 articles about (1R,2S,3aR,5R,7aR,8R)-2-(1-Hydroxy-1-methyl-ethyl)-3a,5-dimethyl-8-o-tolyl-octahydro-1,5-methano-inden-6-one 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: 60.0%

methyl magnesium iodide (917-64-6) + (1R,2S,3aR,5R,7aR,8R)-3a,5-Dimethyl-6-oxo-8-o-tolyl-octahydro-1,5-methano-indene-2-carboxylic acid methyl ester (197306-28-8) → (1R,2S,3aR,5R,7aR,8R)-2-(1-Hydroxy-1-methyl-ethyl)-3a,5-dimethyl-8-o-tolyl-octahydro-1,5-methano-inden-6-one (197306-33-5)

Guidance literature:

In diethyl ether; benzene; for 4h; Heating;

DOI:10.1021/jo9703360

Reference yield:

(1R,4R)-8-Methoxy-1,8-dimethyl-6-o-tolyl-bicyclo[2.2.2]oct-5-en-2-one → (1R,2S,3aR,5R,7aR,8R)-2-(1-Hydroxy-1-methyl-ethyl)-3a,5-dimethyl-8-o-tolyl-octahydro-1,5-methano-inden-6-one (197306-33-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 67.7 percent / BBr₃ / CH₂Cl₂ / 1.5 h / -30 °C

2: 38 percent / Bu₃SnH, AIBN / benzene / 1 h / Heating

3: 60 percent / diethyl ether; benzene / 4 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; boron tribromide; In diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo9703360

Reference yield:

(-)-(1R,4R,8S)-8-bromo-1,8-dimethyl-6-(2-methylphenyl)bicyclo[2.2.2]oct-5-en-2-one (197306-26-6) → (1R,2S,3aR,5R,7aR,8R)-2-(1-Hydroxy-1-methyl-ethyl)-3a,5-dimethyl-8-o-tolyl-octahydro-1,5-methano-inden-6-one (197306-33-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 38 percent / Bu₃SnH, AIBN / benzene / 1 h / Heating

2: 60 percent / diethyl ether; benzene / 4 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In diethyl ether; benzene;

DOI:10.1021/jo9703360

upstream raw materials:

methyl magnesium iodide

(1R,2S,3aR,5R,7aR,8R)-3a,5-Dimethyl-6-oxo-8-o-tolyl-octahydro-1,5-methano-indene-2-carboxylic acid methyl ester

(-)-(1R,4R,8S)-8-bromo-1,8-dimethyl-6-(2-methylphenyl)bicyclo[2.2.2]oct-5-en-2-one

Downstream raw materials:

(+)-(1R,2R,3R,6R,7R)-1,6-dimethyl-4-isopropylidene-2-(2-methylphenyl)tricyclo[4.3.1.0^3,7]decan-9-one

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