(1R,3S,4S)-tert-butyl 3-((S)-1-cyano-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)-2-azabicyclo [2.2.1]heptane-2-carboxylate

Base Information

Chemical Name:(1R,3S,4S)-tert-butyl 3-((S)-1-cyano-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)-2-azabicyclo [2.2.1]heptane-2-carboxylate
CAS No.:1428666-32-3
Molecular Formula:C₂₇H₃₈BN₃O₅
Molecular Weight:495.427
Hs Code.:

Synonyms:(1R,3S,4S)-tert-butyl 3-((S)-1-cyano-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)-2-azabicyclo [2.2.1]heptane-2-carboxylate

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Chemical Property of (1R,3S,4S)-tert-butyl 3-((S)-1-cyano-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)-2-azabicyclo [2.2.1]heptane-2-carboxylate

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Technology Process of (1R,3S,4S)-tert-butyl 3-((S)-1-cyano-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)-2-azabicyclo [2.2.1]heptane-2-carboxylate

There total 5 articles about (1R,3S,4S)-tert-butyl 3-((S)-1-cyano-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)-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: 43.0%

: 1428666-31-2
(1R,3S,4S)-tert-butyl 3-((S)-2-(4-bromophenyl)-1-cyanoethylcarbamoyl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

: 73183-34-3
bis(pinacol)diborane

: 1428666-32-3
(1R,3S,4S)-tert-butyl 3-((S)-1-cyano-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)-2-azabicyclo [2.2.1]heptane-2-carboxylate

Guidance literature:: With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium acetate; In N,N-dimethyl-formamide; at 100 ℃; for 0.666667h; Inert atmosphere;

Reference yield:

: 62129-39-9,79561-82-3
4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine

: 1428666-32-3
(1R,3S,4S)-tert-butyl 3-((S)-1-cyano-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)-2-azabicyclo [2.2.1]heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 4-methyl-morpholine / N,N-dimethyl-formamide / 0.75 h / 20 °C

1.2: 72 h / 0 °C

2.1: trifluoroacetic acid / dichloromethane; water / 3 h

3.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h

3.2: 3 h

4.1: Burgess Reagent / dichloromethane / 3.5 h

5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 0.67 h / 100 °C / Inert atmosphere

With 4-methyl-morpholine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; Burgess Reagent; potassium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

: 869569-99-3
tert-butyl (S)-(1-amino-3-(4-bromophenyl)-1-oxopropan-2-yl)carbamate

: 1428666-32-3
(1R,3S,4S)-tert-butyl 3-((S)-1-cyano-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)-2-azabicyclo [2.2.1]heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: trifluoroacetic acid / dichloromethane; water / 3 h

2.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h

2.2: 3 h

3.1: Burgess Reagent / dichloromethane / 3.5 h

4.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 0.67 h / 100 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; Burgess Reagent; potassium acetate; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide;