(1R,1'S)-Octahydro-1-(2'-iodo-1'-Methylethyl)-7a-Methyl-inden-4-one

Base Information

• Chemical Name: (1R,1'S)-Octahydro-1-(2'-iodo-1'-Methylethyl)-7a-Methyl-inden-4-one
• CAS No.: 145372-32-3
• Molecular Formula: C13H21IO
• Molecular Weight: 320.214
• Mol file: 145372-32-3.mol

Synonyms:(1R,1'S)-Octahydro-1-(2'-iodo-1'-Methylethyl)-7a-Methyl-inden-4-one;[1R-[1α(S*),3aβ,7aα]]-Octahydro-1-(2-iodo-1-Methylethyl)-7a-Methyl-H-inden-4-one

Chemical Property of (1R,1'S)-Octahydro-1-(2'-iodo-1'-Methylethyl)-7a-Methyl-inden-4-one

Chemical Property:

• PSA: 17.07000
• LogP: 3.84300
• Solubility.: Chloroform, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

(1R,1’S)-Octahydro-1-(2’-iodo-1’-methylethyl)-7a-methyl-inden-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Dihydroxyvitamin D3 and associated metabolites.

Technology Process of (1R,1'S)-Octahydro-1-(2'-iodo-1'-Methylethyl)-7a-Methyl-inden-4-one

There total 2 articles about (1R,1'S)-Octahydro-1-(2'-iodo-1'-Methylethyl)-7a-Methyl-inden-4-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: 90.0%

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol (116535-65-0) → des-A,B-22-iodo-23,24-dinorcholan-8-one (145372-32-3)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1021/jo00053a023

Reference yield:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) → des-A,B-22-iodo-23,24-dinorcholan-8-one (145372-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Ph₃P, imidazole, I₂ / tetrahydrofuran / -20 deg C, 15 min then RT, 1.5 h

2: 90 percent / PDC / CH₂Cl₂ / 6 h / Ambient temperature

With 1H-imidazole; dipyridinium dichromate; iodine; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00053a023

Reference yield: 95.0%

(S)-(Z)-{2-[5-(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyl}diphenylphosphine oxide (100858-27-3) + des-A,B-22-iodo-23,24-dinorcholan-8-one (145372-32-3) → tert-Butyl-{(S)-3-[2-[(1R,3aS,7aR)-1-((S)-2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyloxy}-dimethyl-silane (155582-67-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) -78 deg C, 30 min; 2.) -92 deg C;

DOI:10.1016/S0040-4039(00)76530-0

upstream raw materials:

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

Downstream raw materials:

des-A,B-22-iodo-23,24-dinorchol-8-enyl trifluoromethanesulfonate

tert-Butyl-{(S)-3-[2-[(1R,3aS,7aR)-1-((S)-2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyloxy}-dimethyl-silane

(R)-methyl 5-((1R,3aS,7aR,E)-4-((Z)-2-((S)-5-((tert-butyldimethylsilyl)oxy)-2-methylenecyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)hexanoate

(S)-3-[2-[(1R,3aS,7aR)-1-((S)-2-Iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexanol