(-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

Base Information

• Chemical Name: (-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate
• CAS No.: 93489-96-4
• Molecular Formula: C₁₈H₂₈O₂
• Molecular Weight: 276.419
• Mol file: 93489-96-4.mol

Synonyms:(-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

Chemical Property of (-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

There total 6 articles about (-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate 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: 72.0%

(1R,5R)-2-Oxo-bicyclo[3.1.0]hexane-1-carboxylic acid (1S,2R)-2-isopropyl-5-methyl-cyclohexyl ester (74965-61-0,74985-54-9) → (1R,5R)-2-Methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1S,2R)-2-isopropyl-5-methyl-cyclohexyl ester (93489-96-4)

Guidance literature:

DOI:10.1016/S0040-4039(01)90995-5

Reference yield:

(-)-menthol (2216-51-5) → (-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate (93489-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / 4-(dimethylamino)pyridine (DMAP), dicyclohexylcarbodi-imide (DCC) / CH₂Cl₂ / 1.) 0 deg C, 2.) room temperature, 2.5 h

2: 1.) sodium 2-methylbutan-2-olate / 1.) toluene, 0 deg C; room temperature, 2 h, 2.) toluene, room temperature, 2 h

With dmap; sodium tert-pentoxide; dicyclohexyl-carbodiimide; In dichloromethane;

Reference yield:

2-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester (61996-11-0) → (-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate (93489-96-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / potassium hydroxide, water / methanol / 0.33 h / Ambient temperature

2: 50 percent / 4-(dimethylamino)pyridine (DMAP), dicyclohexylcarbodi-imide (DCC) / CH₂Cl₂ / 1.) 0 deg C, 2.) room temperature, 2.5 h

3: 1.) sodium 2-methylbutan-2-olate / 1.) toluene, 0 deg C; room temperature, 2 h, 2.) toluene, room temperature, 2 h

With dmap; potassium hydroxide; water; sodium tert-pentoxide; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

upstream raw materials:

(1R,5R)-2-Oxo-bicyclo[3.1.0]hexane-1-carboxylic acid (1S,2R)-2-isopropyl-5-methyl-cyclohexyl ester

methyl triphenylphosphonium bromide

(-)-menthyl (1R,5R)-2-oxobicyclo<3.1.0>hexane-1-carboxylate

trimethylsilylmethyllithium

Downstream raw materials:

(1R,3S,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

calcitriol

(1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

(1R,5S)-2-Methylene-3-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Refernces

• 1、 Wilson, Stephen R.,Venkatesan,Augelli-Szafran,Yasmin. "A new synthetic route to 1,25-dihydroxy-vitamin D3". . p. 2339 - 2342. Retrieved 2007/10/02.