tert-butyl [(S)-4-((4-chlorobenzyl)amino)-1-oxo-1-(piperidin-1-yl)butan-2-yl]carbamate

Base Information

• Chemical Name: tert-butyl [(S)-4-((4-chlorobenzyl)amino)-1-oxo-1-(piperidin-1-yl)butan-2-yl]carbamate
• CAS No.: 1011735-56-0
• Molecular Formula: C₂₁H₃₂ClN₃O₃
• Molecular Weight: 409.956
• Mol file: 1011735-56-0.mol

Synonyms:tert-butyl [(S)-4-((4-chlorobenzyl)amino)-1-oxo-1-(piperidin-1-yl)butan-2-yl]carbamate

Chemical Property of tert-butyl [(S)-4-((4-chlorobenzyl)amino)-1-oxo-1-(piperidin-1-yl)butan-2-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl [(S)-4-((4-chlorobenzyl)amino)-1-oxo-1-(piperidin-1-yl)butan-2-yl]carbamate

There total 4 articles about tert-butyl [(S)-4-((4-chlorobenzyl)amino)-1-oxo-1-(piperidin-1-yl)butan-2-yl]carbamate 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%

4-chlorobenzaldehyde (104-88-1) + tert-butyl [(1S)-3-amino-1-(piperidin-1-ylcarbonyl)propyl]carbamate (518063-49-5) → tert-butyl [(S)-4-((4-chlorobenzyl)amino)-1-oxo-1-(piperidin-1-yl)butan-2-yl]carbamate (1011735-56-0)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 0 - 20 ℃;

DOI:10.1080/00397910701693633

Reference yield:

(2S)-4-amino-2-[(tert-butoxycarbonyl)amino]butanoic acid (25691-37-6,80445-78-9) → tert-butyl [(S)-4-((4-chlorobenzyl)amino)-1-oxo-1-(piperidin-1-yl)butan-2-yl]carbamate (1011735-56-0)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dioxane; H₂O

2: triethylamine; TBTU / dimethylformamide / 20 °C

3: H₂; Pd/C; CH₃COOH / methanol

4: PS-cyanoborohydride; AcOH / CH₂Cl₂

With palladium on activated charcoal; PS-cyanoborohydride; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; triethylamine; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm031122f

Reference yield:

(2S)-4-(benzyloxycarbonyl)amino-2-(tert-butoxycarbonyl)aminobutyric acid (3350-20-7,47461-65-4,70882-68-7) → tert-butyl [(S)-4-((4-chlorobenzyl)amino)-1-oxo-1-(piperidin-1-yl)butan-2-yl]carbamate (1011735-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; TBTU / dimethylformamide / 20 °C

2: H₂; Pd/C; CH₃COOH / methanol

3: PS-cyanoborohydride; AcOH / CH₂Cl₂

With palladium on activated charcoal; PS-cyanoborohydride; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm031122f

upstream raw materials:

4-chlorobenzaldehyde

tert-butyl [(1S)-3-amino-1-(piperidin-1-ylcarbonyl)propyl]carbamate

(2S)-4-(benzyloxycarbonyl)amino-2-(tert-butoxycarbonyl)aminobutyric acid

(2S)-4-amino-2-[(tert-butoxycarbonyl)amino]butanoic acid

Downstream raw materials:

(3S)-N¹-(4-chlorobenzyl)-4-oxo-4-(piperidin-1-yl)butane-1,3-diamine dihydrochloride

[3-[(4-chloro-benzyl)-methyl-amino]-1-(piperidine-1-carbonyl)-propyl]-carbamic acid tert-butyl ester