acetic acid {3-[(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-2-oxo-1,2,3,6-tetrahydropyridin-3-yl]propyl} ester

Base Information

Chemical Name:acetic acid {3-[(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-2-oxo-1,2,3,6-tetrahydropyridin-3-yl]propyl} ester
CAS No.:898831-91-9
Molecular Formula:C₂₀H₂₆INO₅
Molecular Weight:487.335
Hs Code.:

Synonyms:acetic acid {3-[(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-2-oxo-1,2,3,6-tetrahydropyridin-3-yl]propyl} ester

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Chemical Property of acetic acid {3-[(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-2-oxo-1,2,3,6-tetrahydropyridin-3-yl]propyl} ester

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Technology Process of acetic acid {3-[(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-2-oxo-1,2,3,6-tetrahydropyridin-3-yl]propyl} ester

There total 7 articles about acetic acid {3-[(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-2-oxo-1,2,3,6-tetrahydropyridin-3-yl]propyl} 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: 95.5%

: 898831-77-1
(5S,6S)-1-(2,4-dimethoxybenzyl)-5-diphenylphosphoryloxy-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

: 62116-24-9
3-acetoxypropyl iodide

: 898831-91-9
acetic acid {3-[(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-2-oxo-1,2,3,6-tetrahydropyridin-3-yl]propyl} ester

Guidance literature:: 3-acetoxypropyl iodide; With zinc; In tetrahydrofuran; at 20 ℃; for 2h;

With lithium chloride; In tetrahydrofuran; at -78 - 0 ℃;

(5S,6S)-1-(2,4-dimethoxybenzyl)-5-diphenylphosphoryloxy-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one; In tetrahydrofuran; at -78 - 0 ℃;
DOI:10.1021/jo0606002

Reference yield:

: 898831-83-9
(2S,3S)-2-(tert-butyldimethylsilanyloxy)-3-(2,4-dimethoxybenzylamino)butyric acid ethyl ester

: 898831-91-9
acetic acid {3-[(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-2-oxo-1,2,3,6-tetrahydropyridin-3-yl]propyl} ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 80.1 percent / (i-Pr)2NEt / CH₂Cl₂ / 10 h / 20 °C

2.1: NaOEt / ethanol / 2.5 h / 0 - 20 °C

2.2: H₂O / acetonitrile / 2 h / Heating

3.1: 448 mg / Et₃N / CH₂Cl₂ / 12 h / 20 °C

4.1: (Me₃Sn)2; LiCl / PdCl₂[P(o-tolyl)3]2 / tetrahydrofuran / 0.33 h / 50 °C

4.2: 154 mg / iodine / CH₂Cl₂ / 12 h / 20 °C

5.1: TBAF / tetrahydrofuran / 1 h / 0 °C

6.1: 64.8 mg / pyridine / 12 h / 20 °C

7.1: Zn / tetrahydrofuran / 2 h / 20 °C

7.2: LiCl; CuCN / tetrahydrofuran / -78 - 0 °C

7.3: 95.5 percent / tetrahydrofuran / -78 - 0 °C

With pyridine; tetrabutyl ammonium fluoride; sodium ethanolate; hexamethyldistannane; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; zinc; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jo0606002

Reference yield:

: 1026532-72-8
(5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(2,4-dimethoxy-benzyl)-6-methyl-piperidine-2,4-dione

: 898831-91-9
acetic acid {3-[(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-2-oxo-1,2,3,6-tetrahydropyridin-3-yl]propyl} ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 448 mg / Et₃N / CH₂Cl₂ / 12 h / 20 °C

2.1: (Me₃Sn)2; LiCl / PdCl₂[P(o-tolyl)3]2 / tetrahydrofuran / 0.33 h / 50 °C

2.2: 154 mg / iodine / CH₂Cl₂ / 12 h / 20 °C

3.1: TBAF / tetrahydrofuran / 1 h / 0 °C

4.1: 64.8 mg / pyridine / 12 h / 20 °C

5.1: Zn / tetrahydrofuran / 2 h / 20 °C

5.2: LiCl; CuCN / tetrahydrofuran / -78 - 0 °C

5.3: 95.5 percent / tetrahydrofuran / -78 - 0 °C

With pyridine; tetrabutyl ammonium fluoride; hexamethyldistannane; triethylamine; lithium chloride; zinc; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo0606002