(6S,3aR)-5-(2,4-dimethoxybenzyl)-6-methyl-2,3,3a,5,6-pentahydro-5-azainden-4-one

Base Information

Chemical Name:(6S,3aR)-5-(2,4-dimethoxybenzyl)-6-methyl-2,3,3a,5,6-pentahydro-5-azainden-4-one
CAS No.:898831-94-2
Molecular Formula:C₁₈H₂₃NO₃
Molecular Weight:301.386
Hs Code.:

Synonyms:(6S,3aR)-5-(2,4-dimethoxybenzyl)-6-methyl-2,3,3a,5,6-pentahydro-5-azainden-4-one

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Chemical Property of (6S,3aR)-5-(2,4-dimethoxybenzyl)-6-methyl-2,3,3a,5,6-pentahydro-5-azainden-4-one

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Technology Process of (6S,3aR)-5-(2,4-dimethoxybenzyl)-6-methyl-2,3,3a,5,6-pentahydro-5-azainden-4-one

There total 13 articles about (6S,3aR)-5-(2,4-dimethoxybenzyl)-6-methyl-2,3,3a,5,6-pentahydro-5-azainden-4-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:

: (3S,6S)-3-[3-(9-Bora-bicyclo[3.3.1]non-9-yl)-propyl]-1-(2,4-dimethoxy-benzyl)-4-iodo-6-methyl-3,6-dihydro-1H-pyridin-2-one

: 898831-94-2
(6S,3aR)-5-(2,4-dimethoxybenzyl)-6-methyl-2,3,3a,5,6-pentahydro-5-azainden-4-one

Guidance literature:: With cesium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 50 ℃; for 3.5h;
DOI:10.1021/jo0606002

Reference yield:

: (5S,6S)-1-(2,4-Dimethoxy-benzyl)-5-hydroxy-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one

: 898831-94-2
(6S,3aR)-5-(2,4-dimethoxybenzyl)-6-methyl-2,3,3a,5,6-pentahydro-5-azainden-4-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 64.8 mg / pyridine / 12 h / 20 °C

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

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

2.3: 95.5 percent / tetrahydrofuran / -78 - 0 °C

3.1: 80.8 percent / Ti(i-PrO)4 / ethanol / 1 h / Heating

4.1: 83.1 percent / pyridine; tributylphosphine / 1.5 h / 20 °C

5.1: 99.9 percent / aq. H₂O₂ / tetrahydrofuran / 3 h / 20 °C

6.1: tetrahydrofuran / 7 h / 20 °C

7.1: 170 mg / CsF / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide / 3.5 h / 50 °C

With pyridine; titanium(IV) isopropylate; tributylphosphine; dihydrogen peroxide; cesium fluoride; zinc; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 7.1: Suzuki reaction;
DOI:10.1021/jo0606002

Reference yield:

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

: 898831-94-2
(6S,3aR)-5-(2,4-dimethoxybenzyl)-6-methyl-2,3,3a,5,6-pentahydro-5-azainden-4-one

Guidance literature:: Multi-step reaction with 12 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

10.1: 99.9 percent / aq. H₂O₂ / tetrahydrofuran / 3 h / 20 °C

11.1: tetrahydrofuran / 7 h / 20 °C

12.1: 170 mg / CsF / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide / 3.5 h / 50 °C

With pyridine; titanium(IV) isopropylate; tributylphosphine; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium ethanolate; hexamethyldistannane; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; lithium chloride; zinc; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 12.1: Suzuki reaction;
DOI:10.1021/jo0606002