rel-(2S,4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)-2-hydroxyoctahydro-4H-quinolizin-6-one

Base Information

Chemical Name:rel-(2S,4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)-2-hydroxyoctahydro-4H-quinolizin-6-one
CAS No.:80696-96-4
Molecular Formula:C₁₇H₂₂BrNO₄
Molecular Weight:384.27
Hs Code.:

Synonyms:rel-(2S,4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)-2-hydroxyoctahydro-4H-quinolizin-6-one

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Chemical Property of rel-(2S,4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)-2-hydroxyoctahydro-4H-quinolizin-6-one

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Technology Process of rel-(2S,4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)-2-hydroxyoctahydro-4H-quinolizin-6-one

There total 8 articles about rel-(2S,4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)-2-hydroxyoctahydro-4H-quinolizin-6-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: 14.0%

: 80696-95-3
rel-(4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)octahydro-4H-quinolizin-2,6-dione

: 80696-94-2
rel-(2R,4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)-2-hydroxyoctahydro-4H-quinolizin-6-one

: 80696-96-4
rel-(2S,4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)-2-hydroxyoctahydro-4H-quinolizin-6-one

Guidance literature:: With sodium tetrahydroborate; In N,N-dimethyl-formamide; at -15 ℃; for 1h;
DOI:10.1021/jo00347a036

Reference yield:

: 23068-91-9
methyl 5,5-dimethoxyvalerate

: 80696-96-4
rel-(2S,4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)-2-hydroxyoctahydro-4H-quinolizin-6-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) trimethylaluminum / 1.) dichloromethane + heptane, RT, 30 min, 2.) reflux, 20 h

2: formic acid / CH₂Cl₂ / 4 h / Ambient temperature

3: 98 percent / 3N aq. sodium hydroxide / methanol / 1.25 h / Ambient temperature

4: 79 percent / Jones reagent / acetone / 1 h / -15 °C

5: 60 percent / sodium borohydride / dimethylformamide / 1 h / -15 °C

With sodium hydroxide; sodium tetrahydroborate; formic acid; jones reagent; trimethylaluminum; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00347a036

Reference yield:

: 5392-10-9
2-bromo-4,5-dimethoxybenzaldehyde

: 80696-96-4
rel-(2S,4S,10R)-4-(6-bromo-3,4-dimethoxyphenyl)-2-hydroxyoctahydro-4H-quinolizin-6-one

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) n-butyllithium, hexamethyldisilazane / 1.) THF, hexane, RT, 1 h, 2.) ether, RT, 20 min

2: 1.) trimethylaluminum / 1.) dichloromethane + heptane, RT, 30 min, 2.) reflux, 20 h

3: formic acid / CH₂Cl₂ / 4 h / Ambient temperature

4: 98 percent / 3N aq. sodium hydroxide / methanol / 1.25 h / Ambient temperature

5: 79 percent / Jones reagent / acetone / 1 h / -15 °C

6: 60 percent / sodium borohydride / dimethylformamide / 1 h / -15 °C

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; formic acid; jones reagent; trimethylaluminum; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00347a036