benzyl (3S,4R)-3-azido-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]piperidine-1-carboxylate

Base Information

Chemical Name:benzyl (3S,4R)-3-azido-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]piperidine-1-carboxylate
CAS No.:1007596-67-9
Molecular Formula:C₁₉H₂₀Cl₂N₆O₃
Molecular Weight:451.312
Hs Code.:

Synonyms:benzyl (3S,4R)-3-azido-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]piperidine-1-carboxylate

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Chemical Property of benzyl (3S,4R)-3-azido-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]piperidine-1-carboxylate

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Technology Process of benzyl (3S,4R)-3-azido-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]piperidine-1-carboxylate

There total 7 articles about benzyl (3S,4R)-3-azido-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]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: 70.0%

: 1007596-66-8
benzyl (3S,4R)-4-amino-3-azidopiperidine-1-carboxylate

: 1007596-67-9
benzyl (3S,4R)-3-azido-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]piperidine-1-carboxylate

Guidance literature:: 3,4-di-chloro-5-methyl-1H-pyrrole-2-carboxylic acid; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; for 0.5h;

benzyl (3S,4R)-4-amino-3-azidopiperidine-1-carboxylate; In N,N-dimethyl-formamide;

Reference yield:

: 1007596-65-7
benzyl (3S,4R)-3-azido-4-(benzhydrylideneamino)piperidine-1-carboxylate

: 1007596-67-9
benzyl (3S,4R)-3-azido-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / water; tetrahydrofuran / 12 h / 20 °C

2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h

With pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1021/jm500462x

Reference yield:

: (+/-)-trans-benzyl 4-amino-3-hydroxypiperdine-1-carboxylate

: 1007596-67-9
benzyl (3S,4R)-3-azido-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: chiral column Column: AD 250 / Resolution of racemate

2.1: toluene / 12 h / Reflux

3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 °C

3.2: 12 h / 20 °C

4.1: pyridinium p-toluenesulfonate / water; tetrahydrofuran / 12 h / 20 °C

5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h

With di-isopropyl azodicarboxylate; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm500462x