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

Base Information

• Chemical Name: 7(S)-hydroxy-2(S)-(4-methoxy-benzyl)-8(S)-methyl-3-oxo-octahydro-imidazo[1,5-a]pyridine-5(R)-carbaldehyde
• CAS No.: 732278-68-1
• Molecular Formula: C₁₇H₂₂N₂O₄
• Molecular Weight: 318.373
• Mol file: 732278-68-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about 7(S)-hydroxy-2(S)-(4-methoxy-benzyl)-8(S)-methyl-3-oxo-octahydro-imidazo[1,5-a]pyridine-5(R)-carbaldehyde 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: 75.0%

(5R,7S,8R,8aS)-7-hydroxy-5-hydroxymethyl-2-(4-methoxybenzyl)-8-methylhexahydroimidazo[1,5-a]pyridin-3-one (732278-69-2) → 7(S)-hydroxy-2(S)-(4-methoxy-benzyl)-8(S)-methyl-3-oxo-octahydro-imidazo[1,5-a]pyridine-5(R)-carbaldehyde (732278-68-1)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; methanesulfonic acid; [bis(acetoxy)iodo]benzene; In chloroform-d1; for 3h;

DOI:10.1002/anie.200454208

Reference yield:

(5R)-(but-2-enyl)-4-oxy-5,6-dihydro-[1,4]oxazin-2-one (334994-42-2) → 7(S)-hydroxy-2(S)-(4-methoxy-benzyl)-8(S)-methyl-3-oxo-octahydro-imidazo[1,5-a]pyridine-5(R)-carbaldehyde (732278-68-1)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene / 2.5 h / 200 °C

2: 87 percent / DIBAL-H / CH₂Cl₂; toluene / -78 - 20 °C

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

4: 19 mg / acetonitrile / 0.5 h

5: 75 percent / TEMPO; PhI(OAc)2; Me₃SO₃H / CDCl₃ / 3 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; trimethoxythioether; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In chloroform-d1; dichloromethane; ethyl acetate; toluene; acetonitrile;

DOI:10.1016/j.tet.2006.02.044

Reference yield:

2-(R,E)-aminohex-4-en-1-ol (334994-40-0) → 7(S)-hydroxy-2(S)-(4-methoxy-benzyl)-8(S)-methyl-3-oxo-octahydro-imidazo[1,5-a]pyridine-5(R)-carbaldehyde (732278-68-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 63 percent / (i-Pr)2NEt / acetonitrile / 4 h

2: 84 percent / mCPBA; Na₂HPO₄ / CH₂Cl₂ / 0.5 h / -78 °C

3: toluene / 2.5 h / 200 °C

4: 87 percent / DIBAL-H / CH₂Cl₂; toluene / -78 - 20 °C

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

6: 19 mg / acetonitrile / 0.5 h

7: 75 percent / TEMPO; PhI(OAc)2; Me₃SO₃H / CDCl₃ / 3 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; disodium hydrogenphosphate; [bis(acetoxy)iodo]benzene; trimethoxythioether; hydrogen; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In chloroform-d1; dichloromethane; ethyl acetate; toluene; acetonitrile;

DOI:10.1016/j.tet.2006.02.044

upstream raw materials:

(5R,7S,8R,8aS)-7-hydroxy-5-hydroxymethyl-2-(4-methoxybenzyl)-8-methylhexahydroimidazo[1,5-a]pyridin-3-one

(E)-(R)-2-Amino-hex-4-enoic acid methyl ester

4-methoxy-benzylamine

2-(R,E)-aminohex-4-en-1-ol

Downstream raw materials:

(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

(5S,7S,8R,8aS)-2-(4-methoxybenzyl)-8-methyl-5-(2-nitroethyl)-3-oxooctahydroimidazo[1,5-a]pyridin-7-yl acetate