tert-butyl (2S)-2-{(S)-hydroxy[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2S)-2-{(S)-hydroxy[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperidine-1-carboxylate
CAS No.:1007109-85-4
Molecular Formula:C₂₃H₃₆BNO₅
Molecular Weight:417.354
Hs Code.:

Synonyms:tert-butyl (2S)-2-{(S)-hydroxy[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperidine-1-carboxylate

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Chemical Property of tert-butyl (2S)-2-{(S)-hydroxy[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperidine-1-carboxylate

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Technology Process of tert-butyl (2S)-2-{(S)-hydroxy[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperidine-1-carboxylate

There total 6 articles about tert-butyl (2S)-2-{(S)-hydroxy[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperidine-1-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: 91.0%

: 1007110-00-0
tert-butyl (2S)-2-[(S)-hydroxy{3-[(trifluoromethanesulfonyl)oxy]phenyl}methyl]piperidine-1-carboxylate

: 73183-34-3
bis(pinacol)diborane

: 1007109-85-4
tert-butyl (2S)-2-{(S)-hydroxy[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperidine-1-carboxylate

Guidance literature:: With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; dimethyl sulfoxide; at 80 ℃; for 3h;
DOI:10.1248/cpb.c16-00314

Reference yield:

: 53087-13-1
3-(benzyloxy)phenyl bromide

: 1007109-85-4
tert-butyl (2S)-2-{(S)-hydroxy[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: magnesium; iodine / tetrahydrofuran / 2 h / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Inert atmosphere

2.1: hydrogen; 5%-palladium/activated carbon / methanol

3.1: pyridine / chloroform / 2 h / 0 - 20 °C

4.1: L-Selectride / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane; dimethyl sulfoxide / 3 h / 80 °C

With pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 5%-palladium/activated carbon; hydrogen; iodine; potassium acetate; L-Selectride; magnesium; In tetrahydrofuran; 1,4-dioxane; methanol; chloroform; dimethyl sulfoxide;
DOI:10.1248/cpb.c16-00314

Reference yield:

: 1007109-99-0
tert-butyl (2S)-2-(3-hydroxybenzoyl)piperidine-1-carboxylate

: 1007109-85-4
tert-butyl (2S)-2-{(S)-hydroxy[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / chloroform / 2 h / 0 - 20 °C

2: L-Selectride / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane; dimethyl sulfoxide / 3 h / 80 °C

With pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; L-Selectride; In tetrahydrofuran; 1,4-dioxane; chloroform; dimethyl sulfoxide;
DOI:10.1248/cpb.c16-00314