(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3-[3-(2-nitrophenylselanyl)propyl]-3,6-dihydro-1H-pyridin-2-one

Base Information

Chemical Name:(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3-[3-(2-nitrophenylselanyl)propyl]-3,6-dihydro-1H-pyridin-2-one
CAS No.:898831-93-1
Molecular Formula:C₂₄H₂₇IN₂O₅Se
Molecular Weight:629.353
Hs Code.:

Synonyms:(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3-[3-(2-nitrophenylselanyl)propyl]-3,6-dihydro-1H-pyridin-2-one

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Chemical Property of (3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3-[3-(2-nitrophenylselanyl)propyl]-3,6-dihydro-1H-pyridin-2-one

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Technology Process of (3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3-[3-(2-nitrophenylselanyl)propyl]-3,6-dihydro-1H-pyridin-2-one

There total 10 articles about (3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3-[3-(2-nitrophenylselanyl)propyl]-3,6-dihydro-1H-pyridin-2-one 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: 83.1%

: 898831-96-4
(3S,6S)-1-(2,4-dimethoxybenzyl)-3-(3-hydroxypropyl)-4-iodo-6-methyl-3,6-dihydro-1H-pyridin-2-one

: 51694-22-5
ortho-nitrophenyl selenocyanate

: 898831-93-1
(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3-[3-(2-nitrophenylselanyl)propyl]-3,6-dihydro-1H-pyridin-2-one

Guidance literature:: With pyridine; tributylphosphine; at 20 ℃; for 1.5h;
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

: 898831-93-1
(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3-[3-(2-nitrophenylselanyl)propyl]-3,6-dihydro-1H-pyridin-2-one

Guidance literature:: Multi-step reaction with 7 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

6.1: 80.8 percent / Ti(i-PrO)4 / ethanol / 1 h / Heating

7.1: 83.1 percent / pyridine; tributylphosphine / 1.5 h / 20 °C

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

Reference yield:

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

: 898831-93-1
(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3-[3-(2-nitrophenylselanyl)propyl]-3,6-dihydro-1H-pyridin-2-one

Guidance literature:: Multi-step reaction with 9 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

8.1: 80.8 percent / Ti(i-PrO)4 / ethanol / 1 h / Heating

9.1: 83.1 percent / pyridine; tributylphosphine / 1.5 h / 20 °C

With pyridine; titanium(IV) isopropylate; tributylphosphine; 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