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

Base Information

• Chemical Name: [3-[(4-chloro-benzyl)-methyl-amino]-1-(piperidine-1-carbonyl)-propyl]-carbamic acid tert-butyl ester
• CAS No.: 1011735-57-1
• Molecular Formula: C₂₂H₃₄ClN₃O₃
• Molecular Weight: 423.983

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

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

Chemical Property:

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

There total 5 articles about [3-[(4-chloro-benzyl)-methyl-amino]-1-(piperidine-1-carbonyl)-propyl]-carbamic acid tert-butyl 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: 84.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + tert-butyl [(S)-4-((4-chlorobenzyl)amino)-1-oxo-1-(piperidin-1-yl)butan-2-yl]carbamate (1011735-56-0) → [3-[(4-chloro-benzyl)-methyl-amino]-1-(piperidine-1-carbonyl)-propyl]-carbamic acid tert-butyl ester (1011735-57-1)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 10 - 20 ℃; for 16h;

DOI:10.1080/00397910701693633

Reference yield:

(2S)-4-amino-2-[(tert-butoxycarbonyl)amino]butanoic acid (25691-37-6,80445-78-9) → [3-[(4-chloro-benzyl)-methyl-amino]-1-(piperidine-1-carbonyl)-propyl]-carbamic acid tert-butyl ester (1011735-57-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dioxane; H₂O

2.1: triethylamine; TBTU / dimethylformamide / 20 °C

3.1: H₂; Pd/C; CH₃COOH / methanol

4.1: CH₃COOH; NaCNBH₃ / methanol

4.2: NaCNBH₃; AcOH

With palladium on activated charcoal; hydrogen; sodium cyanoborohydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; triethylamine; In 1,4-dioxane; methanol; 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) → [3-[(4-chloro-benzyl)-methyl-amino]-1-(piperidine-1-carbonyl)-propyl]-carbamic acid tert-butyl ester (1011735-57-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine; TBTU / dimethylformamide / 20 °C

2.1: H₂; Pd/C; CH₃COOH / methanol

3.1: CH₃COOH; NaCNBH₃ / methanol

3.2: NaCNBH₃; AcOH

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

DOI:10.1021/jm031122f

upstream raw materials:

formaldehyd

4-chlorobenzaldehyde

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

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

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