ethyl (1S,2R,3R)-2-(tert-butoxycarbonylamino)-3-fluorocyclohexanecarboxylate

Base Information

• Chemical Name: ethyl (1S,2R,3R)-2-(tert-butoxycarbonylamino)-3-fluorocyclohexanecarboxylate
• CAS No.: 1337970-95-2
• Molecular Formula: C₁₄H₂₄FNO₄
• Molecular Weight: 289.347
• Mol file: 1337970-95-2.mol

Synonyms:ethyl (1S,2R,3R)-2-(tert-butoxycarbonylamino)-3-fluorocyclohexanecarboxylate

Chemical Property of ethyl (1S,2R,3R)-2-(tert-butoxycarbonylamino)-3-fluorocyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1S,2R,3R)-2-(tert-butoxycarbonylamino)-3-fluorocyclohexanecarboxylate

There total 7 articles about ethyl (1S,2R,3R)-2-(tert-butoxycarbonylamino)-3-fluorocyclohexanecarboxylate 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: 41.0%

ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohexanecarboxylate (1337970-94-1) → ethyl (1S,2S)-2-(tert-butoxycarbonylamino)yclohex-3-enecarboxylate (1201815-26-0) + ethyl (1S,2R,3R)-2-(tert-butoxycarbonylamino)-3-fluorocyclohexanecarboxylate (1337970-95-2)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; toluene; at 0 ℃; for 6h; Inert atmosphere;

DOI:10.1039/c1ob05648d

Reference yield:

(1R,2S)-2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylic acid (870288-16-7,233600-33-4) → ethyl (1S,2S)-2-(tert-butoxycarbonylamino)yclohex-3-enecarboxylate (1201815-26-0) + ethyl (1S,2R,3R)-2-(tert-butoxycarbonylamino)-3-fluorocyclohexanecarboxylate (1337970-95-2)

Guidance literature:

Multi-step reaction with 5 steps

1: iodine; sodium hydrogencarbonate; potassium iodide / dichloromethane; water / 16 h / 20 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 6 h / 65 °C

3: sodium ethanolate / 9 h / 20 °C

4: palladium 10% on activated carbon; ammonium acetate / ethanol / 2 h / 75 °C

5: diethylamino-sulfur trifluoride / dichloromethane; toluene / 6 h / 0 °C / Inert atmosphere

With diethylamino-sulfur trifluoride; palladium 10% on activated carbon; ammonium acetate; iodine; sodium ethanolate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;

DOI:10.1039/c1ob05648d

Reference yield:

tert-butyl (1R,4R,5S,8R)-4-iodo-7-oxo-6-oxabicyclo[3.2.1]octan-8-ylcarbamate → ethyl (1S,2S)-2-(tert-butoxycarbonylamino)yclohex-3-enecarboxylate (1201815-26-0) + ethyl (1S,2R,3R)-2-(tert-butoxycarbonylamino)-3-fluorocyclohexanecarboxylate (1337970-95-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 6 h / 65 °C

2: sodium ethanolate / 9 h / 20 °C

3: palladium 10% on activated carbon; ammonium acetate / ethanol / 2 h / 75 °C

4: diethylamino-sulfur trifluoride / dichloromethane; toluene / 6 h / 0 °C / Inert atmosphere

With diethylamino-sulfur trifluoride; palladium 10% on activated carbon; ammonium acetate; sodium ethanolate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1039/c1ob05648d

upstream raw materials:

(1R,2S)-2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylic acid

ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohex-4-enecarboxylate

ethyl (1S,2R,3S)-2-(tert-butoxycarbonylamino)-3-hydroxycyclohexanecarboxylate

(1R,2S)-cis-2-aminocyclohex-3-enecarboxylic acid