(5R,7S,8R,8aS)-7-Hydroxy-5-(1-hydroxy-2-nitro-ethyl)-2-(4-methoxy-benzyl)-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one

Base Information

Chemical Name:(5R,7S,8R,8aS)-7-Hydroxy-5-(1-hydroxy-2-nitro-ethyl)-2-(4-methoxy-benzyl)-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one
CAS No.:732278-74-9
Molecular Formula:C₁₈H₂₅N₃O₆
Molecular Weight:379.413
Hs Code.:

Synonyms:(5R,7S,8R,8aS)-7-Hydroxy-5-(1-hydroxy-2-nitro-ethyl)-2-(4-methoxy-benzyl)-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one

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Chemical Property of (5R,7S,8R,8aS)-7-Hydroxy-5-(1-hydroxy-2-nitro-ethyl)-2-(4-methoxy-benzyl)-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one

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Technology Process of (5R,7S,8R,8aS)-7-Hydroxy-5-(1-hydroxy-2-nitro-ethyl)-2-(4-methoxy-benzyl)-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one

There total 13 articles about (5R,7S,8R,8aS)-7-Hydroxy-5-(1-hydroxy-2-nitro-ethyl)-2-(4-methoxy-benzyl)-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-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: 84.0%

: 75-52-5
nitromethane

: 732278-68-1
7(S)-hydroxy-2(S)-(4-methoxy-benzyl)-8(S)-methyl-3-oxo-octahydro-imidazo[1,5-a]pyridine-5(R)-carbaldehyde

: 732278-74-9
(5R,7S,8R,8aS)-7-Hydroxy-5-(1-hydroxy-2-nitro-ethyl)-2-(4-methoxy-benzyl)-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 12h;
DOI:10.1002/anie.200454208

Reference yield:

: 334994-40-0
2-(R,E)-aminohex-4-en-1-ol

: 732278-74-9
(5R,7S,8R,8aS)-7-Hydroxy-5-(1-hydroxy-2-nitro-ethyl)-2-(4-methoxy-benzyl)-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 63 percent / (i-Pr)2NEt / acetonitrile / 4 h

2.1: 84 percent / mCPBA; Na₂HPO₄ / CH₂Cl₂ / 0.5 h / -78 °C

3.1: toluene / 2.5 h / 200 °C

4.1: 87 percent / DIBAL-H / CH₂Cl₂; toluene / -78 - 20 °C

5.1: H₂ / Pd/C / ethyl acetate / 12 h / 760 Torr

6.1: 19 mg / acetonitrile / 0.5 h

7.1: 75 percent / TEMPO; PhI(OAc)2; Me₃SO₃H / CDCl₃ / 3 h

8.1: n-BuLi / tetrahydrofuran / 0.58 h

8.2: 84 percent / tetrahydrofuran / 12 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; disodium hydrogenphosphate; n-butyllithium; [bis(acetoxy)iodo]benzene; trimethoxythioether; hydrogen; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; chloroform-d1; dichloromethane; ethyl acetate; toluene; acetonitrile;
DOI:10.1016/j.tet.2006.02.044

Reference yield:

: 334994-42-2
(5R)-(but-2-enyl)-4-oxy-5,6-dihydro-[1,4]oxazin-2-one

: 732278-74-9
(5R,7S,8R,8aS)-7-Hydroxy-5-(1-hydroxy-2-nitro-ethyl)-2-(4-methoxy-benzyl)-8-methyl-hexahydro-imidazo[1,5-a]pyridin-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene / 2.5 h / 200 °C

2.1: 87 percent / DIBAL-H / CH₂Cl₂; toluene / -78 - 20 °C

3.1: H₂ / Pd/C / ethyl acetate / 12 h / 760 Torr

4.1: 19 mg / acetonitrile / 0.5 h

5.1: 75 percent / TEMPO; PhI(OAc)2; Me₃SO₃H / CDCl₃ / 3 h

6.1: n-BuLi / tetrahydrofuran / 0.58 h

6.2: 84 percent / tetrahydrofuran / 12 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; n-butyllithium; [bis(acetoxy)iodo]benzene; trimethoxythioether; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; chloroform-d1; dichloromethane; ethyl acetate; toluene; acetonitrile;
DOI:10.1016/j.tet.2006.02.044