(1R,2S,5R)-(-)-Menthyl amine

Base Information

• Chemical Name: (1R,2S,5R)-(-)-Menthyl amine
• CAS No.: 34048-57-2
• Molecular Formula: C10H21N
• Molecular Weight: 191.744
• Hs Code.: 2921300090
• Mol file: 34048-57-2.mol

Synonyms:(1R,2S,5R)-(-)-Menthyl amine

Chemical Property of (1R,2S,5R)-(-)-Menthyl amine

Chemical Property:

• PSA: 26.02000
• LogP: 3.90820

Purity/Quality:

98% ^*data from raw suppliers

(1R,2S,5R)-(-)-MENTHYL AMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,2S,5R)-(-)-Menthyl amine

There total 5 articles about (1R,2S,5R)-(-)-Menthyl amine 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: 92.0%

L-menthylamine (2216-54-8,787534-09-2) → (-)-(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexaneammonium chloride (34048-57-2)

Guidance literature:

With hydrogenchloride; In water; for 0.5h;

DOI:10.1007/s11172-008-0054-3

Reference yield: 90.0%

(-)-(1R,3R,4S)-menthyl isocyanate (39633-53-9) → (-)-(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexaneammonium chloride (34048-57-2)

Guidance literature:

With hydrogenchloride; water; In diethyl ether; at 20 ℃;

Reference yield:

(2R,5S)-menthone (10458-14-7,14073-97-3,17627-49-5,7786-64-3) → (-)-(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexaneammonium chloride (34048-57-2)

Guidance literature:

Multi-step reaction with 3 steps

1: hydroxylamine hydrochloride; sodium carbonate / ethanol; water / 120 h / 25 °C

2: sulfuric acid; N,N,N,N',N',N'-hexamethyl-butane-1,4-diammonium dimethylsulfate / methanol; water / 50 °C / Electrochemical reduction

3: hydrogenchloride / diethyl ether / 0 °C

With hydrogenchloride; sulfuric acid; hydroxylamine hydrochloride; sodium carbonate; N,N,N,N',N',N'-hexamethyl-butane-1,4-diammonium dimethylsulfate; In methanol; diethyl ether; ethanol; water;

DOI:10.1002/anie.201101330

upstream raw materials:

(-)-(1R,3R,4S)-menthyl isocyanate

L-menthylamine

(2R,5S)-menthone

(1R,5S)-menthone oxime

Downstream raw materials:

N-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-[1,1'-biphenyl]-4-carboxamide

N-[(1R, 2S, 5R)-2-isopropyl-5-methylcyclohexyl]-4-chlorobenzamide

4-tert-butyl-N-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]benzamide

N-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]-4-methylbenzamide

Refernces

• 1、 Kulisch, Joern,Nieger, Martin,Stecker, Florian,Fischer, Andreas,Waldvogel, Siegfried R.. "Efficient and stereodivergent electrochemical synthesis of optically pure menthylamines". supporting information; experimental part. p. 5564 - 5567. Retrieved 2011/07/30.