(1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol

Base Information

• Chemical Name: (1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol
• CAS No.: 304865-25-6
• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.392
• Mol file: 304865-25-6.mol

Synonyms:(1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol

Chemical Property of (1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol

There total 9 articles about (1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol 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: 98.0%

dimethyl sulfate (77-78-1) + (1'S,2'R)-6-(2'-hydroxymethyl-1',2'-dimethylcyclopentyl)-2-methoxy-4-methylphenol (304859-77-6) → (1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol (304865-25-6)

Guidance literature:

With potassium carbonate; In acetone; for 48h;

DOI:10.1021/ja001455r

Reference yield:

5-iodovaniline (5438-36-8) → (1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol (304865-25-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaBH₄; NaOH / methanol / 0 - 20 °C

2.1: (CBrCl₂)2; PPh₃ / CH₂Cl₂ / 0 - 20 °C

3.1: 3.60 g / LiAlH₄ / CH₂Cl₂; diethyl ether / 2.5 h / 20 °C

4.1: 79 percent / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 24.5 h / 20 °C

5.1: PPh₃; NaOAc / Pd(OAc)2 / dimethylformamide / 120 °C

5.2: 72 percent / H₂ / Pd/C / ethanol / 12 h / atmospheric pressure

6.1: BH₃*THF; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza...

7.1: 97 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

8.1: 98 percent / K₂CO₃ / acetone / 48 h

With dmap; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; borane-THF; 1,2-dibromo-1,1,2,2-tetrachloroethane; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza..; sodium acetate; potassium carbonate; dicyclohexyl-carbodiimide; triphenylphosphine; palladium diacetate; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; 5.1: Heck reaction / 6.1: Corey-Bakshi-Shibata reduction;

DOI:10.1021/ja001455r

Reference yield:

4-hydroxy-3-iodo-5-methoxybenzyl alcohol (37987-21-6) → (1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol (304865-25-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (CBrCl₂)2; PPh₃ / CH₂Cl₂ / 0 - 20 °C

2.1: 3.60 g / LiAlH₄ / CH₂Cl₂; diethyl ether / 2.5 h / 20 °C

3.1: 79 percent / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 24.5 h / 20 °C

4.1: PPh₃; NaOAc / Pd(OAc)2 / dimethylformamide / 120 °C

4.2: 72 percent / H₂ / Pd/C / ethanol / 12 h / atmospheric pressure

5.1: BH₃*THF; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza...

6.1: 97 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

7.1: 98 percent / K₂CO₃ / acetone / 48 h

With dmap; lithium aluminium tetrahydride; borane-THF; 1,2-dibromo-1,1,2,2-tetrachloroethane; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza..; sodium acetate; potassium carbonate; dicyclohexyl-carbodiimide; triphenylphosphine; palladium diacetate; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; 4.1: Heck reaction / 5.1: Corey-Bakshi-Shibata reduction;

DOI:10.1021/ja001455r

upstream raw materials:

dimethyl sulfate

(1'S,2'R)-6-(2'-hydroxymethyl-1',2'-dimethylcyclopentyl)-2-methoxy-4-methylphenol

4-hydroxy-3-iodo-5-methoxybenzyl alcohol

5-iodovaniline

Downstream raw materials:

(1R,2R)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentyl-1-carbaldehyde

(S)-5-methyl-3-(1,2,2-trimethylcyclopentyl)benzene-1,2-diol

(1'S)-2-methoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)phenol

(1'S)-1,2-dimethoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)benzene