N,N'-bis[(S)-2-hydroxy(2-phenyl)ethyl]-(1R,2R)-1,2-diaminocyclohexane

Base Information

• Chemical Name: N,N'-bis[(S)-2-hydroxy(2-phenyl)ethyl]-(1R,2R)-1,2-diaminocyclohexane
• CAS No.: 371145-86-7
• Molecular Formula: C₂₂H₃₀N₂O₂
• Molecular Weight: 354.492
• Mol file: 371145-86-7.mol

Synonyms:N,N'-bis[(S)-2-hydroxy(2-phenyl)ethyl]-(1R,2R)-1,2-diaminocyclohexane

Chemical Property of N,N'-bis[(S)-2-hydroxy(2-phenyl)ethyl]-(1R,2R)-1,2-diaminocyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N'-bis[(S)-2-hydroxy(2-phenyl)ethyl]-(1R,2R)-1,2-diaminocyclohexane

There total 6 articles about N,N'-bis[(S)-2-hydroxy(2-phenyl)ethyl]-(1R,2R)-1,2-diaminocyclohexane 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: 70.05%

N,N'-dibenzyl-N,N'-bis[(S)-2-hydroxy(2-phenyl)ethyl]-(1R,2R)-1,2-diaminocyclo-hexane → N,N'-bis[(S)-2-hydroxy(2-phenyl)ethyl]-(1R,2R)-1,2-diaminocyclohexane (371145-86-7)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In methanol;

DOI:10.1016/j.tetasy.2017.09.014

Reference yield: 32.0%

(S)-2-Hydroxy-N-[(1R,2R)-2-((S)-2-hydroxy-2-phenyl-acetylamino)-cyclohexyl]-2-phenyl-acetamide → N,N'-bis[(S)-2-hydroxy(2-phenyl)ethyl]-(1R,2R)-1,2-diaminocyclohexane (371145-86-7)

Guidance literature:

With dimethylsulfide borane complex; triethyloxonium fluoroborate; In tetrahydrofuran;

DOI:10.1016/S0957-4166(01)00290-7

Reference yield:

(1R,2R)-1,2-diaminocyclohexane (20439-47-8) → N,N'-bis[(S)-2-hydroxy(2-phenyl)ethyl]-(1R,2R)-1,2-diaminocyclohexane (371145-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 56 percent / N-hydroxysuccinimide; 1,3-dicyclohexylcarbodiimide / tetrahydrofuran / 48 h / 20 °C

2.1: boron trifluoride etherate / tetrahydrofuran / Heating

2.2: borane-dimethyl sulfide complex / tetrahydrofuran / 18 h / Heating

2.3: 32 percent / hydrochloric acid / 1 h / Heating

With 1-hydroxy-pyrrolidine-2,5-dione; boron trifluoride diethyl etherate; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1016/j.tet.2004.11.030

upstream raw materials:

(S)-Mandelic acid

(1R,2R)-1,2-diaminocyclohexane

(1R,2R)-N,N'-dibenzylcyclohexane-1,2-diamine

(R,R)-N,N′-bis(phenylmethylene)-1,2-cyclohexanediamine