(1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Base Information

Chemical Name:(1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
CAS No.:1256387-75-3
Molecular Formula:C₃₀H₃₈BN₃O₄
Molecular Weight:515.46
Hs Code.:

Synonyms:(1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

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Chemical Property of (1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

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Technology Process of (1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

There total 6 articles about (1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-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: 85.0%

: 1256387-74-2
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

: 99770-93-1
benzene-1,4-diboronic acid bispinacol ester

: 1256387-75-3
(1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; water; at 90 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jm401499g

Reference yield:

: 1256387-73-1
3-(2-amino-4-bromo-phenylcarbamoyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

: 1256387-75-3
(1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: ethanol / 130 - 170 °C / Sealed tube

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,2-dimethoxyethane / 4 h / 90 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; ethanol; water; 2: |Suzuki Coupling;
DOI:10.1021/jm401499g

Reference yield:

: (1R,3S,4S)-methyl 2-((R)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate

: 1256387-75-3
(1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: palladium on carbon; hydrogen / ethanol; methanol / 15 h / 30 - 35 °C / 5171.62 Torr

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3.5 h / 8 - 20 °C

3: lithium hydroxide / methanol; tetrahydrofuran; water / 0.08 h

4: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C

5: ethanol / 130 - 170 °C / Sealed tube

6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,2-dimethoxyethane / 4 h / 90 °C / Inert atmosphere

With 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium on carbon; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 6: |Suzuki Coupling;
DOI:10.1021/jm401499g