(2R,3R,αR,E)-methyl 6-oxo-1-(α-methylbenzyl)-2-styrylpiperidine-3-carboxylate

Base Information

Chemical Name:(2R,3R,αR,E)-methyl 6-oxo-1-(α-methylbenzyl)-2-styrylpiperidine-3-carboxylate
CAS No.:1318759-07-7
Molecular Formula:C₂₃H₂₅NO₃
Molecular Weight:363.456
Hs Code.:

Synonyms:(2R,3R,αR,E)-methyl 6-oxo-1-(α-methylbenzyl)-2-styrylpiperidine-3-carboxylate

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Chemical Property of (2R,3R,αR,E)-methyl 6-oxo-1-(α-methylbenzyl)-2-styrylpiperidine-3-carboxylate

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Technology Process of (2R,3R,αR,E)-methyl 6-oxo-1-(α-methylbenzyl)-2-styrylpiperidine-3-carboxylate

There total 5 articles about (2R,3R,αR,E)-methyl 6-oxo-1-(α-methylbenzyl)-2-styrylpiperidine-3-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: 48.0%

: 1318759-06-6
(4R,5R,αR,E)-4-methoxycarbonyl-5-(N-α-methylbenzylamino)-7-phenyl-hept-6-enoic acid

: 1318759-07-7
(2R,3R,αR,E)-methyl 6-oxo-1-(α-methylbenzyl)-2-styrylpiperidine-3-carboxylate

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.04.015

Reference yield:

: (4R,5R,αR,6E)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-7-phenyl-hept-6-enoic acid

: 1318759-07-7
(2R,3R,αR,E)-methyl 6-oxo-1-(α-methylbenzyl)-2-styrylpiperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: ammonium cerium (IV) nitrate; water / acetonitrile / 0.67 h / Inert atmosphere

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

With ammonium cerium (IV) nitrate; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tetasy.2011.04.015

Reference yield:

: 124957-40-0
(E)-methyl 3-acetoxy-2-methylene-5-phenyl-pent-4-enoate

: 1318759-07-7
(2R,3R,αR,E)-methyl 6-oxo-1-(α-methylbenzyl)-2-styrylpiperidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

2.3: Inert atmosphere

3.1: ammonium cerium (IV) nitrate; water / acetonitrile / 0.67 h / Inert atmosphere

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

With n-butyllithium; ammonium cerium (IV) nitrate; N-benzyl-N,N,N-triethylammonium chloride; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; cesium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tetasy.2011.04.015