2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol

Base Information

• Chemical Name: 2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol
• CAS No.: 1312714-85-4
• Molecular Formula: C₂₃H₃₅NO₂
• Molecular Weight: 357.536

Synonyms:2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol

Chemical Property of 2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol

Chemical Property:

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• Pictogram(s):  
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Technology Process of 2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol

There total 4 articles about 2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol 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: 88.0%

3-tert-butyl-5-methylsalicylaldehyde (41715-31-5) + (1S,2S,3R,5S)-2-amino-3-hydroxymethyl-2,6,6-trimethylbicyclo[3.1.1]heptane (327611-65-4) → 2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol (1312714-85-4)

Guidance literature:

With magnesium sulfate; In methanol; at 20 ℃; for 24h;

DOI:10.1016/j.tetasy.2011.03.013

Reference yield:

ethyl (1S,2S,3R,5S)-2-amino-2,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylate (327611-64-3) → 2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol (1312714-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / Reflux

2: magnesium sulfate / methanol / 24 h / 20 °C

With lithium aluminium tetrahydride; magnesium sulfate; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetasy.2011.03.013

Reference yield:

(+)-α-pinene (7785-70-8,25766-18-1) → 2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol (1312714-85-4)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium hydroxide; sodium sulfite / 48 h / 20 °C

2: hydrogenchloride / 12 h / Reflux

3: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / Reflux

4: magnesium sulfate / methanol / 24 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; magnesium sulfate; potassium hydroxide; sodium sulfite; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetasy.2011.03.013

upstream raw materials:

(1S,2S,5R,7S)-2,8,8-trimethyl-3-azatricyclo[5.1.1.0^2,5]nonan-4-one

3-tert-butyl-5-methylsalicylaldehyde

(1S,2S,3R,5S)-2-amino-3-hydroxymethyl-2,6,6-trimethylbicyclo[3.1.1]heptane

(+)-α-pinene

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