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

Base Information

• Chemical Name: {4-[(1α,5α,6α)-6-(tert-butyldimethylsilanyloxy)-3-azabicyclo[3.1.0]hex-3-yl]-3,5-difluorophenyl}carbamic acid benzyl ester
• CAS No.: 681425-46-7
• Molecular Formula: C₂₅H₃₂F₂N₂O₃Si
• Molecular Weight: 474.623
• Mol file: 681425-46-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

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) + benzyl chloroformate (501-53-1,94274-21-2) → {4-[(1α,5α,6α)-6-(tert-butyldimethylsilanyloxy)-3-azabicyclo[3.1.0]hex-3-yl]-3,5-difluorophenyl}carbamic acid benzyl ester (681425-46-7)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jm058204j

Reference yield:

6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (681425-42-3) → {4-[(1α,5α,6α)-6-(tert-butyldimethylsilanyloxy)-3-azabicyclo[3.1.0]hex-3-yl]-3,5-difluorophenyl}carbamic acid benzyl ester (681425-46-7)

Guidance literature:

Multi-step reaction with 6 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

6.1: 0.078 g / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 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-[(1α,5α,6α)-6-(tert-butyldimethylsilanyloxy)-3-azabicyclo[3.1.0]hex-3-yl]-3,5-difluorophenyl}carbamic acid benzyl ester (681425-46-7)

Guidance literature:

Multi-step reaction with 5 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

5: 0.078 g / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 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:

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

benzyl chloroformate

(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