(2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester
• CAS No.: 916914-48-2
• Molecular Formula: C₂₈H₃₅BrN₂O₅
• Molecular Weight: 559.5
• Mol file: 916914-48-2.mol

Synonyms:(2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester

Chemical Property of (2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester

There total 1 articles about (2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl 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: 25.0%

(2S,5S,6S)-6-(4-Bromo-phenyl)-5-methyl-1-(2,2,2-trifluoro-acetyl)-piperidine-2-carboxylic acid methyl ester (916914-44-8) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester (916914-48-2)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; at 20 ℃; for 24h;

DOI:10.1021/jo061758p

Reference yield:

(2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester (916914-48-2) → (2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester (1026201-47-7)

Guidance literature:

Multi-step reaction with 3 steps

1: TMSOTf; 2,6-lutidine / 0.25 h / 0 °C

2: 675 mg / NaBH₄ / methanol / 0.67 h / 0 °C

3: CuI; PPh₃; Et₃N / Pd(PPh₃)4 / dimethylformamide / 15 h / 90 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; triethylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; N,N-dimethyl-formamide; 3: Sonogashira reaction;

DOI:10.1021/jo061758p

Reference yield:

(2S,5S,6S)-6-(4-Bromo-phenyl)-1-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-5-methyl-piperidine-2-carboxylic acid methyl ester (916914-48-2) → (2S,5S,6S)-6-(4-(3-(dimethylamino)prop-1-ynyl)phenyl)-5-methylpiperidine-2-carboxylic acid (916914-60-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: TMSOTf; 2,6-lutidine / 0.25 h / 0 °C

2.1: 675 mg / NaBH₄ / methanol / 0.67 h / 0 °C

3.1: CuI; PPh₃; Et₃N / Pd(PPh₃)4 / dimethylformamide / 15 h / 90 °C

4.1: Amberlyst A₂₆ hydroxide resin / tetrahydrofuran; H₂O; methanol

4.2: AcOH / H₂O

With 2,6-dimethylpyridine; sodium tetrahydroborate; copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; Amberlyst A₂₆ hydroxide resin; triethylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 3.1: Sonogashira reaction;

DOI:10.1021/jo061758p

upstream raw materials:

(2S,5S,6S)-6-(4-Bromo-phenyl)-5-methyl-1-(2,2,2-trifluoro-acetyl)-piperidine-2-carboxylic acid methyl ester

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

(2S,5S,6S)-6-(4-Bromo-phenyl)-5-methyl-1-(2,2,2-trifluoro-acetyl)-piperidine-2-carboxylic acid methyl ester

methyl (2S,5S,6S)-6-(4-bromophenyl)-5-methylpiperidine-2-carboxylate

(2S,5S,6S)-6-(4-bromophenyl)-5-methylpiperidine-2-carboxylic acid

(2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester