(1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol

Base Information

• Chemical Name: (1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol
• CAS No.: 681425-44-5
• Molecular Formula: C₁₁H₁₀F₂N₂O₃
• Molecular Weight: 256.209
• Mol file: 681425-44-5.mol

Synonyms:(1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol

Chemical Property of (1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol

There total 3 articles about (1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol 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:

(1α,5α,6α)-3-azabicyclo[3.1.0]hexan-1-ol (862713-83-5) + 3,4,5-trifluoronitrobenzene (66684-58-0) → (1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol (681425-44-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50 ℃; for 12h;

DOI:10.1021/jm058204j

Reference yield:

6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (681425-42-3) → (1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol (681425-44-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / 0.17 h / -95 °C

1.2: catechol borane / tetrahydrofuran / 16 h / 50 °C

1.3: 15 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 18 h

2.1: 100 percent / H₂ / Pd(OH)2/C / methanol / 3 h

3.1: 0.070 g / diisopropylethylamine / dimethylformamide / 12 h / 50 °C

With n-butyllithium; hydrogen; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm058204j

Reference yield:

(1α,5α,6α)-6-hydroxy-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (504438-12-4,1255099-53-6) → (1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol (681425-44-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd(OH)2/C / methanol / 3 h

2: 0.070 g / diisopropylethylamine / dimethylformamide / 12 h / 50 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm058204j

upstream raw materials:

(1α,5α,6α)-3-azabicyclo[3.1.0]hexan-1-ol

3,4,5-trifluoronitrobenzene

6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

(1α,5α,6α)-6-hydroxy-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

Downstream raw materials:

{4-[(1α,5α,6α)-6-(tert-butyldimethylsilanyloxy)-3-azabicyclo[3.1.0]hex-3-yl]-3,5-difluorophenyl}carbamic acid benzyl ester

4-[(1S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-aza-bicyclo[3.1.0]hex-3-yl]-3,5-difluoro-phenylamine

(1α,5α,6α)-6-(tert-butyldimethylsilyloxy)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexane