(1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

Base Information

• Chemical Name: (1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate
• CAS No.: 1430745-37-1
• Molecular Formula: C₂₃H₃₂F₂N₂O₄
• Molecular Weight: 438.515
• Mol file: 1430745-37-1.mol

Synonyms:(1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

Chemical Property of (1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

There total 5 articles about (1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate 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: 21.2%

3,4,5-trifluoropyridine (67815-54-7) + (1R,3s,5S)-tert-butyl 3-((1r,4R)-4-hydroxycyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1430747-30-0) → (1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1430745-37-1) + (1R,3s,5S)-tert-butyl 3-((1s,4S)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1430747-32-2)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 0.5h; Inert atmosphere; Cooling with ice;

Reference yield:

4-Benzyloxyphenol (103-16-2) → (1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1430745-37-1) + (1R,3s,5S)-tert-butyl 3-((1s,4S)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1430747-32-2)

Guidance literature:

Multi-step reaction with 4 steps

1: di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice

2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 3 h / 20 °C / 1140.08 Torr

3: sodium tetraborate decahydrate; palladium 10% on activated carbon; hydrogen / isopropyl alcohol / 24 h / 80 °C / 9000.9 Torr / Autoclave

4: potassium tert-butylate / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice

With sodium tetraborate decahydrate; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; isopropyl alcohol;

Reference yield:

(1R,3s,5S)-tert-butyl 3-(4-hydroxyphenoxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1430746-08-9) → (1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1430745-37-1) + (1R,3s,5S)-tert-butyl 3-((1s,4S)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1430747-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetraborate decahydrate; palladium 10% on activated carbon; hydrogen / isopropyl alcohol / 24 h / 80 °C / 9000.9 Torr / Autoclave

2: potassium tert-butylate / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice

With sodium tetraborate decahydrate; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; In tetrahydrofuran; isopropyl alcohol;

upstream raw materials:

(1R,3s,5S)-tert-butyl 3-(4-hydroxyphenoxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

3,4,5-trifluoropyridine

(1R,3s,5S)-tert-butyl 3-((1r,4R)-4-hydroxycyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

(1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate