Acetic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Base Information

• Chemical Name: Acetic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester
• CAS No.: 372947-58-5
• Molecular Formula: C₂₅H₃₀O₂
• Molecular Weight: 362.512

Synonyms:Acetic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property of Acetic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

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Technology Process of Acetic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

There total 6 articles about Acetic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 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)-exo]-3-exo-(diphenylmethyl)borneol (87420-27-7) + acetyl chloride (75-36-5) → Acetic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (372947-58-5)

Guidance literature:

With sodium hydride; In 1,4-dioxane;

DOI:10.1021/ol016566p DOI:10.1021/jo026183k

Reference yield:

(1R,4S)-1,7,7-trimethyl-2-(trimethylsilyloxy)bicyclo[2.2.1]hept-2-en (70982-26-2) → Acetic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (372947-58-5)

Guidance literature:

Multi-step reaction with 3 steps

1: TiCl₄ / CH₂Cl₂ / 1 h / -50 °C

2: 5.6 g / LAH / tetrahydrofuran / 6 h / 20 °C

3: 90 percent / NaH / dioxane

With lithium aluminium tetrahydride; titanium tetrachloride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1021/jo026183k

Reference yield:

diphenylchloromethane (90-99-3) → Acetic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (372947-58-5)

Guidance literature:

Multi-step reaction with 3 steps

1: TiCl₄ / CH₂Cl₂ / 1 h / -50 °C

2: 5.6 g / LAH / tetrahydrofuran / 6 h / 20 °C

3: 90 percent / NaH / dioxane

With lithium aluminium tetrahydride; titanium tetrachloride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1021/jo026183k

upstream raw materials:

[(1R)-exo]-3-exo-(diphenylmethyl)borneol

acetyl chloride

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

(1R,4S)-1,7,7-trimethyl-2-(trimethylsilyloxy)bicyclo[2.2.1]hept-2-en

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