(5S,6S)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone

Base Information

• Chemical Name: (5S,6S)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone
• CAS No.: 1261298-20-7
• Molecular Formula: C₁₈H₂₅NO₂
• Molecular Weight: 287.402
• Mol file: 1261298-20-7.mol

Synonyms:(5S,6S)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone

Chemical Property of (5S,6S)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone

There total 1 articles about (5S,6S)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone 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: 77.0%

(3S, 8S, 8aR)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine + allyl-trimethyl-silane (762-72-1) → (5S,6S)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone (1261298-20-7) + (5S,6R)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone (1394931-23-7)

Guidance literature:

(3S, 8S, 8aR)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.25h;

allyl-trimethyl-silane; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1039/c2ob25392e

Reference yield: 69.0%

(5S,6S)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone (1261298-20-7) + allyl bromide (106-95-6) → (5S,6S)-6-allyl-1-[((S)-2-(allyloxy)-1-phenylethyl)]-5-ethylpiperidin-2-one (1394931-30-6) + (5S,6S)-6-allyl-5-ethyl-2-piperidone (1394931-13-5)

Guidance literature:

(5S,6S)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone; With oxygen; sodium hydroxide; In tert-butyl methyl ether; at 40 ℃; for 24h;

allyl bromide; In tert-butyl methyl ether; at 20 ℃; for 19h;

DOI:10.1039/c2ob25392e

Reference yield:

(5S,6S)-6-allyl-5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-2-piperidone (1261298-20-7) → (1S,4S,9aS)-1-ethyl-4-propylquinolizidine (1394931-17-9,247233-76-7) + (1S,4R,9aS)-1-ethyl-4-propylquinolizidine (1394931-33-9,247233-76-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxygen; sodium hydroxide / tert-butyl methyl ether / 24 h / 40 °C

1.2: 19 h / 20 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8 h / 20 °C

3.1: 10% Pd/C; hydrogen / methanol / 18 h

4.1: cerium(III) chloride / tetrahydrofuran / 1 h / 20 °C

4.2: 18 h / 20 °C

4.3: 0.5 h / -78 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; cerium(III) chloride; 10% Pd/C; hydrogen; oxygen; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; tert-butyl methyl ether;

DOI:10.1039/c2ob25392e

upstream raw materials:

allyl-trimethyl-silane

Downstream raw materials:

(1S,4S,9aS)-1-ethyl-4-propylquinolizidine

(1S,4R,9aS)-1-ethyl-4-propylquinolizidine

(5S,6S)-6-allyl-1-[((S)-2-(allyloxy)-1-phenylethyl)]-5-ethylpiperidin-2-one

(5S,6S)-6-allyl-5-ethyl-2-piperidone