(2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal

Base Information

• Chemical Name: (2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal
• CAS No.: 908290-21-1
• Molecular Formula: C₁₉H₂₇NO₃
• Molecular Weight: 317.428
• Mol file: 908290-21-1.mol

Synonyms:(2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal

Chemical Property of (2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal

There total 5 articles about (2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal 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:

C19H25NO3 (908290-19-7) → (2S,3aS,7aS)-1-benzyl-2-[(1'S)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal (908290-22-2) + (2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal (908290-21-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -20 ℃; for 6h;

DOI:10.1021/jo060592p

Reference yield:

(2S,3R,4aS,8aS)-1-benzyl-3-hydroxy-2-methyl-7-oxodecahydroquinoline ethylene acetal (908290-43-7) → (2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal (908290-21-1)

Guidance literature:

(2S,3R,4aS,8aS)-1-benzyl-3-hydroxy-2-methyl-7-oxodecahydroquinoline ethylene acetal; With trifluoroacetic anhydride;

With triethylamine; In tetrahydrofuran; for 8h; Heating;

With sodium hydroxide; In tetrahydrofuran; water;

DOI:10.1021/jo060592p

Reference yield:

methyl (2S,3aS,7aS)-1-benzyl-6-oxooctahydroindole-2-carboxylate ethylene acetal (908290-15-3) → (2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal (908290-21-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 0.5 h

1.2: i-PrMgCl / tetrahydrofuran / 0.67 h / cooling

2.1: tetrahydrofuran; diethyl ether / 1 h / 0 °C

3.1: 1.05 g / NaBH₄ / methanol / 6 h / -20 °C

With sodium tetrahydroborate; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1021/jo060592p

upstream raw materials:

C₁₉H₂₅NO₃

(2S,3R,4aS,8aS)-1-benzyl-3-hydroxy-2-methyl-7-oxodecahydroquinoline ethylene acetal

methyl (2S,3aS,7aS)-1-benzyl-6-oxooctahydroindole-2-carboxylate ethylene acetal

methyl (2S,3aS,7aS)-1-benzyl-6-oxo-octahydroindole-2-carboxylate

Downstream raw materials:

(2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-chloroethyl]octahydroindol-6-one ethylene acetal

(2S,3R,4aS,8aS)-1-benzyl-3-hydroxy-2-methyl-7-oxodecahydroquinoline ethylene acetal