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

Base Information

• Chemical Name: 4-[(1S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-aza-bicyclo[3.1.0]hex-3-yl]-3,5-difluoro-phenylamine
• CAS No.: 681425-47-8
• Molecular Formula: C₁₇H₂₆F₂N₂OSi
• Molecular Weight: 340.489
• Mol file: 681425-47-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 4-[(1S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-aza-bicyclo[3.1.0]hex-3-yl]-3,5-difluoro-phenylamine 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)-6-(tert-butyldimethylsilyloxy)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexane (681425-45-6) → 4-[(1S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-aza-bicyclo[3.1.0]hex-3-yl]-3,5-difluoro-phenylamine (681425-47-8)

Guidance literature:

With iron; ammonium chloride; In ethanol; Heating;

DOI:10.1021/jm058204j

Reference yield:

6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (681425-42-3) → 4-[(1S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-aza-bicyclo[3.1.0]hex-3-yl]-3,5-difluoro-phenylamine (681425-47-8)

Guidance literature:

Multi-step reaction with 5 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

4.1: 88 percent / imidazole / CH₂Cl₂ / 3 h

5.1: Fe; aq. NH₄Cl / ethanol / Heating

With 1H-imidazole; n-butyllithium; hydrogen; iron; ammonium chloride; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; 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) → 4-[(1S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-aza-bicyclo[3.1.0]hex-3-yl]-3,5-difluoro-phenylamine (681425-47-8)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 88 percent / imidazole / CH₂Cl₂ / 3 h

4: Fe; aq. NH₄Cl / ethanol / Heating

With 1H-imidazole; hydrogen; iron; ammonium chloride; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm058204j

upstream raw materials:

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

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

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