tert-butyl (1R,4r)-4-[(R)-1-(2-nitrophenylsulfonyl)aziridin-2-yl]cyclohexylcarbamate

Base Information

• Chemical Name: tert-butyl (1R,4r)-4-[(R)-1-(2-nitrophenylsulfonyl)aziridin-2-yl]cyclohexylcarbamate
• CAS No.: 1373311-88-6
• Molecular Formula: C₁₉H₂₇N₃O₆S
• Molecular Weight: 425.506
• Mol file: 1373311-88-6.mol

Synonyms:tert-butyl (1R,4r)-4-[(R)-1-(2-nitrophenylsulfonyl)aziridin-2-yl]cyclohexylcarbamate

Chemical Property of tert-butyl (1R,4r)-4-[(R)-1-(2-nitrophenylsulfonyl)aziridin-2-yl]cyclohexylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (1R,4r)-4-[(R)-1-(2-nitrophenylsulfonyl)aziridin-2-yl]cyclohexylcarbamate

There total 9 articles about tert-butyl (1R,4r)-4-[(R)-1-(2-nitrophenylsulfonyl)aziridin-2-yl]cyclohexylcarbamate 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: 65.0%

tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate (1372805-36-1) → tert-butyl (1R,4r)-4-[(R)-1-(2-nitrophenylsulfonyl)aziridin-2-yl]cyclohexylcarbamate (1373311-88-6)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -5 - 20 ℃; for 1.6h; Inert atmosphere;

DOI:10.1055/s-0031-1289724

Reference yield:

trans-tert-butyl 4-(1-(2-nitrophenylsulfonyl)aziridin-2-yl)-cyclohexylcarbamate → tert-butyl (1R,4r)-4-[(R)-1-(2-nitrophenylsulfonyl)aziridin-2-yl]cyclohexylcarbamate (1373311-88-6) + (S)-trans-tert-butyl 4-(1-(2-nitrophenylsulfonyl)aziridin-2-yl)-cyclohexylcarbamate

Guidance literature:

With Chiralcel OJ; In hexane; isopropyl alcohol; Resolution of racemate;

DOI:10.1016/j.bmc.2014.07.040

Reference yield:

methyl (R)-2-[(1s,4S)-4-hydroxycyclohexyl]-2-(2-nitrophenylsulfonamido)acetate (1372805-32-7) → tert-butyl (1R,4r)-4-[(R)-1-(2-nitrophenylsulfonyl)aziridin-2-yl]cyclohexylcarbamate (1373311-88-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 1.5 h / 5 - 20 °C / Inert atmosphere; Large scale reaction

2.1: sodium azide / N,N-dimethyl-formamide / 16 h / 55 °C / Large scale reaction

3.1: triphenylphosphine / ethyl acetate / 1.5 h / 65 °C / Large scale reaction

3.2: 1.5 h / 65 °C / Large scale reaction

4.1: triethylamine / dichloromethane / 18 h / 25 °C / Large scale reaction

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 2.5 h / -10 - 0 °C / Inert atmosphere

6.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1.6 h / -5 - 20 °C / Inert atmosphere

With sodium azide; di-isopropyl azodicarboxylate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-0031-1289724

upstream raw materials:

methyl (R)-2-[(1s,4S)-4-hydroxycyclohexyl]-2-(2-nitrophenylsulfonamido)acetate

methyl (R)-2-[(1s,4S)-4-(methylsulfonyloxy)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate

tert-butyl (1R,4r)-4-[(R)-2-hydroxy-1-(2-nitrophenylsulfonamido)ethyl]cyclohexylcarbamate

D-4-hydroxyphenylglycine