(6S,6aS,8aR,8bS)-6a-Ethyl-1-hydroxy-6-methoxy-8a-phenyl-octahydro-cyclopenta[hi]indolizine-4,8-dione

Base Information

Chemical Name:(6S,6aS,8aR,8bS)-6a-Ethyl-1-hydroxy-6-methoxy-8a-phenyl-octahydro-cyclopenta[hi]indolizine-4,8-dione
CAS No.:220502-09-0
Molecular Formula:C₁₉H₂₃NO₄
Molecular Weight:329.396
Hs Code.:

Synonyms:(6S,6aS,8aR,8bS)-6a-Ethyl-1-hydroxy-6-methoxy-8a-phenyl-octahydro-cyclopenta[hi]indolizine-4,8-dione

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Chemical Property of (6S,6aS,8aR,8bS)-6a-Ethyl-1-hydroxy-6-methoxy-8a-phenyl-octahydro-cyclopenta[hi]indolizine-4,8-dione

Chemical Property:

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Technology Process of (6S,6aS,8aR,8bS)-6a-Ethyl-1-hydroxy-6-methoxy-8a-phenyl-octahydro-cyclopenta[hi]indolizine-4,8-dione

There total 8 articles about (6S,6aS,8aR,8bS)-6a-Ethyl-1-hydroxy-6-methoxy-8a-phenyl-octahydro-cyclopenta[hi]indolizine-4,8-dione 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: 66.0%

: 220502-08-9
((4S,4aS,7R,7aR)-4a-Ethyl-4-methoxy-2,6-dioxo-7-phenyl-octahydro-[1]pyrindin-1-yl)-acetaldehyde

: 220502-09-0
(6S,6aS,8aR,8bS)-6a-Ethyl-1-hydroxy-6-methoxy-8a-phenyl-octahydro-cyclopenta[hi]indolizine-4,8-dione

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 25 ℃;
DOI:10.1016/S0040-4039(98)02510-6

Reference yield:

: 220502-01-2
(R)-2-Benzyl-4-ethyl-5-methoxy-4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-cyclohexa-2,5-dienone

: 220502-09-0
(6S,6aS,8aR,8bS)-6a-Ethyl-1-hydroxy-6-methoxy-8a-phenyl-octahydro-cyclopenta[hi]indolizine-4,8-dione

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) H₂; 2.) Li, NH₃; 3.) piperylene / 1.) 5 percent Pd/C / 1.) THF, 60 psi; 2.) THF, t-BuOH, -78 deg C; 3.) THF

2: 72 percent / m-CPBA / CH₂Cl₂

3: 95 percent / TsOH / benzene; H₂O / Heating

4: 62 percent / CH₂Cl₂; 1,2-dichloro-ethane / 0 °C

5: 1.) LiBH₄; 2.) ClCOCOCl, DMSO; 3.) Et₃N / 1.) MeOH, THF; 2.) CH₂Cl₂, -78 deg C; 3.) CH₂Cl₂, -78 deg C to 25 deg C

6: TfOH / CH₂Cl₂ / 12 h / 0 °C

7: 1.) O₃; 2.) Me₂S / 1.) CH₂Cl₂; 2.) CH₂Cl₂

8: 66 percent / TsOH / CH₂Cl₂ / 25 °C

With lithium borohydride; oxalyl dichloride; penta-1,3-diene; dimethylsulfide; trifluorormethanesulfonic acid; ammonia; hydrogen; lithium; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In dichloromethane; water; 1,2-dichloro-ethane; benzene;
DOI:10.1016/S0040-4039(98)02510-6

Reference yield:

: 220502-04-5
(S)-3-((3R,5S)-5-Benzyl-3-ethyl-2-oxo-tetrahydro-furan-3-yl)-3-methoxy-propionic acid

: 220502-09-0
(6S,6aS,8aR,8bS)-6a-Ethyl-1-hydroxy-6-methoxy-8a-phenyl-octahydro-cyclopenta[hi]indolizine-4,8-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / CH₂Cl₂; 1,2-dichloro-ethane / 0 °C

2: 1.) LiBH₄; 2.) ClCOCOCl, DMSO; 3.) Et₃N / 1.) MeOH, THF; 2.) CH₂Cl₂, -78 deg C; 3.) CH₂Cl₂, -78 deg C to 25 deg C

3: TfOH / CH₂Cl₂ / 12 h / 0 °C

4: 1.) O₃; 2.) Me₂S / 1.) CH₂Cl₂; 2.) CH₂Cl₂

5: 66 percent / TsOH / CH₂Cl₂ / 25 °C

With lithium borohydride; oxalyl dichloride; dimethylsulfide; trifluorormethanesulfonic acid; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; In dichloromethane; 1,2-dichloro-ethane;
DOI:10.1016/S0040-4039(98)02510-6