(5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

Base Information

Chemical Name:(5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one
CAS No.:898831-87-3
Molecular Formula:C₂₁H₃₂INO₄Si
Molecular Weight:517.479
Hs Code.:

Synonyms:(5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

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Chemical Property of (5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

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Technology Process of (5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

There total 7 articles about (5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-5,6-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:

: 898831-85-1
(5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one

: 898831-87-3
(5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

Guidance literature:: (5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one; With hexamethyldistannane; lithium chloride; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; at 50 ℃; for 0.333333h;

With iodine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/jo0606002

Reference yield:

: (2S,3S)-3-Amino-2-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester

: 898831-87-3
(5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 4.43 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 10 h / 20 °C

2.1: 80.1 percent / (i-Pr)2NEt / CH₂Cl₂ / 10 h / 20 °C

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

3.2: H₂O / acetonitrile / 2 h / Heating

4.1: 448 mg / Et₃N / CH₂Cl₂ / 12 h / 20 °C

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

5.2: 154 mg / iodine / CH₂Cl₂ / 12 h / 20 °C

With sodium ethanolate; hexamethyldistannane; sodium tris(acetoxy)borohydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; ethanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/jo0606002

Reference yield:

: (2S,3S)-3-Benzylamino-2-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester

: 898831-87-3
(5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: H₂; AcOH / Pd(OH)2/C / ethanol / 2 h / 20 °C

2.1: 4.43 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 10 h / 20 °C

3.1: 80.1 percent / (i-Pr)2NEt / CH₂Cl₂ / 10 h / 20 °C

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

4.2: H₂O / acetonitrile / 2 h / Heating

5.1: 448 mg / Et₃N / CH₂Cl₂ / 12 h / 20 °C

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

6.2: 154 mg / iodine / CH₂Cl₂ / 12 h / 20 °C

With hydrogen; sodium ethanolate; hexamethyldistannane; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium dihydroxide; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; ethanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/jo0606002