TRANS (1S,2S)-1N-CBZ-CYCLOHEXANE-1,2-DIAMINE

Base Information

• Chemical Name: TRANS (1S,2S)-1N-CBZ-CYCLOHEXANE-1,2-DIAMINE
• CAS No.: 199336-05-5
• Molecular Formula: C14H20N2O2
• Molecular Weight: 248.32
• Mol file: 199336-05-5.mol

Synonyms:TRANS (1S,2S)-1N-CBZ-CYCLOHEXANE-1,2-DIAMINE;N-[(1S,2S)-2-aminocyclohexyl]-Carbamic Acid Phenylmethyl Ester

Chemical Property of TRANS (1S,2S)-1N-CBZ-CYCLOHEXANE-1,2-DIAMINE

Chemical Property:

• Boiling Point: 409.5±44.0 °C(Predicted)
• PKA: 12.05±0.40(Predicted)
• PSA: 64.35000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 3.27390

Purity/Quality:

N-[(1S,2S)-2-aminocyclohexyl]-CarbamicAcidPhenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[(1S,2S)-2-aminocyclohexyl]-Carbamic Acid Phenylmethyl Ester is a reagent in the synthesis of the anti-cancer agent AA005 derivatives. also used in the preparation of pirenzepine analogs, as antimuscarinics.

Technology Process of TRANS (1S,2S)-1N-CBZ-CYCLOHEXANE-1,2-DIAMINE

There total 4 articles about TRANS (1S,2S)-1N-CBZ-CYCLOHEXANE-1,2-DIAMINE 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: 97.0%

benzyl tert-butyl ((1S,2S)-cyclohexane-1,2-diyl)dicarbamate → benzyl N-[(1S,2S)-2-aminocyclohexyl]carbamate (199336-05-5,1353973-30-4,445479-92-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1002/ejoc.201403415

Reference yield: 43.0%

(S,S)-1,2-diaminocyclohexane (21436-03-3) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl N-[(1S,2S)-2-aminocyclohexyl]carbamate (199336-05-5,1353973-30-4,445479-92-5)

Guidance literature:

With methanesulfonic acid; potassium acetate; bromocresol green; In 1,2-dimethoxyethane; ethanol; water; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2008.06.025

Reference yield:

tert-butyl ((1S,2S)-2-aminocyclohexyl)carbamate (180683-64-1) → benzyl N-[(1S,2S)-2-aminocyclohexyl]carbamate (199336-05-5,1353973-30-4,445479-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate / water; 1,4-dioxane / 18.5 h / 0 - 25 °C

2: trifluoroacetic acid / dichloromethane / 2 h / 25 °C

With sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water;

DOI:10.1002/ejoc.201403415

upstream raw materials:

(S,S)-1,2-diaminocyclohexane

benzyl chloroformate

tert-butyl ((1S,2S)-2-aminocyclohexyl)carbamate

Downstream raw materials:

{(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-cyclohexyl}-carbamic acid benzyl ester

{(1S,2S)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-cyclohexyl}-carbamic acid benzyl ester

(S)-2-Amino-N-((1S,2S)-2-amino-cyclohexyl)-3-(4-nitro-phenyl)-propionamide

C₂₈H₄₆N₂O₅

Refernces

• 1、 Minarini, Anna,Marucci, Gabriella,Bellucci, Cristina,Giorgi, Gianluca,Tumiatti, Vincenzo,Bolognesi, Maria Laura,Matera, Riccardo,Rosini, Michela,Melchiorre, Carlo. "Design, synthesis, and biological evaluation of pirenzepine analogs bearing a 1,2-cyclohexanediamine and perhydroquinoxaline units in exchange for the piperazine ring as antimuscarinics". . p. 7311 - 7320. Retrieved 2008/12/22.
• 2、 Wu,Kobayashi,Sun,Yoo,Paik,Gansow,Carrasquillo,Pastan,Brechbiel. "Stereochemical influence on the stability of radio-metal complexes in vivo. Synthesis and evaluation of the four stereoisomers of 2-(p- nitrobenzyl)-trans-CyDTPA". . p. 1925 - 1934. Retrieved 2007/10/03.