methyl (hydroxymethyl) ((1R,5R)-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)carbamate

Base Information

• Chemical Name: methyl (hydroxymethyl) ((1R,5R)-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)carbamate
• CAS No.: 1384835-05-5
• Molecular Formula: C₂₀H₂₉NO₅
• Molecular Weight: 363.454

Synonyms:methyl (hydroxymethyl) ((1R,5R)-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)carbamate

Chemical Property of methyl (hydroxymethyl) ((1R,5R)-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl (hydroxymethyl) ((1R,5R)-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)carbamate

There total 6 articles about methyl (hydroxymethyl) ((1R,5R)-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)carbamate 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: 54.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + methyl (1R,5R)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enylcarbamate (1384835-04-4) → methyl (hydroxymethyl) ((1R,5R)-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)carbamate (1384835-05-5)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jo300776d

Reference yield:

C17H24O4S (1384834-98-3) → methyl (hydroxymethyl) ((1R,5R)-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)carbamate (1384835-05-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.67 h / 0 °C / Inert atmosphere

2.2: 6 h / Reflux; Inert atmosphere

3.1: toluene-4-sulfonic acid / methanol; N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere

3.2: 4 h / 150 °C / Inert atmosphere

4.1: potassium tert-butylate / tert-butyl alcohol / 1.5 h / 20 °C / Inert atmosphere

With potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Overman rearrangement / 2.2: Overman rearrangement;

DOI:10.1021/jo300776d

Reference yield:

(1S,5S)-5-((S)-2-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enol (552289-36-8) → methyl (hydroxymethyl) ((1R,5R)-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)carbamate (1384835-05-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine; dmap / chloroform / 30 h / 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

2.2: 16 h / 0 - 20 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.67 h / 0 °C / Inert atmosphere

3.2: 6 h / Reflux; Inert atmosphere

4.1: toluene-4-sulfonic acid / methanol; N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere

4.2: 4 h / 150 °C / Inert atmosphere

5.1: potassium tert-butylate / tert-butyl alcohol / 1.5 h / 20 °C / Inert atmosphere

With pyridine; dmap; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Overman rearrangement / 3.2: Overman rearrangement;

DOI:10.1021/jo300776d

upstream raw materials:

formaldehyd

methyl (1R,5R)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enylcarbamate

C₁₇H₂₄O₄S

(1S,5S)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enol

Downstream raw materials:

(2aR,2a⁽¹⁾R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate

C₂₈H₃₉NO₉S

2-(((methoxycarbonyl) ((1R,5R)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-en-1-yl)amino)methyl)-3-oxocyclopent-1-en-1-yl acetate

(2aR,2a⁽¹⁾R,6aS,8R,9aR)methyl 8-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyl-3,6-dioxododecahydro-1H-cyclohepta[cd]indole-1-carboxylate

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