(3S,7R,8R,9aR)-8-(3-hydroxyphenyl)-7,8-dimethyl-3-phenyl-hexahydro-1H-quinolizin-4(6H)-one

Base Information

Chemical Name:(3S,7R,8R,9aR)-8-(3-hydroxyphenyl)-7,8-dimethyl-3-phenyl-hexahydro-1H-quinolizin-4(6H)-one
CAS No.:918423-47-9
Molecular Formula:C₂₃H₂₇NO₂
Molecular Weight:349.473
Hs Code.:

Synonyms:(3S,7R,8R,9aR)-8-(3-hydroxyphenyl)-7,8-dimethyl-3-phenyl-hexahydro-1H-quinolizin-4(6H)-one

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Chemical Property of (3S,7R,8R,9aR)-8-(3-hydroxyphenyl)-7,8-dimethyl-3-phenyl-hexahydro-1H-quinolizin-4(6H)-one

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Technology Process of (3S,7R,8R,9aR)-8-(3-hydroxyphenyl)-7,8-dimethyl-3-phenyl-hexahydro-1H-quinolizin-4(6H)-one

There total 7 articles about (3S,7R,8R,9aR)-8-(3-hydroxyphenyl)-7,8-dimethyl-3-phenyl-hexahydro-1H-quinolizin-4(6H)-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: 59.0%

: 918423-45-7
(7R,8R,9aR)-8-(3-(benzyloxy)phenyl)-7,8-dimethyl-3-phenyl-7,8,9,9α-tetrahydro-1H-quinolizin-4(6H)-one

: 918423-47-9
(3S,7R,8R,9aR)-8-(3-hydroxyphenyl)-7,8-dimethyl-3-phenyl-hexahydro-1H-quinolizin-4(6H)-one

: 918423-48-0
(3R,7R,8R,9aR)-8-(3-hydroxyphenyl)-7,8-dimethyl-3-phenyl-hexahydro-1H-quinolizin-4(6H)-one

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 16h;
DOI:10.1021/jm060486f

Reference yield:

: 918423-39-9
(2R,4R,5R)-2-allyl-4-(3-(benzyloxy)phenyl)-4,5-dimethyl-piperidine

: 918423-47-9
(3S,7R,8R,9aR)-8-(3-hydroxyphenyl)-7,8-dimethyl-3-phenyl-hexahydro-1H-quinolizin-4(6H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 74 percent / N,N-diisopropylethylamine; O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium*BF₄ / acetonitrile / 16 h / 20 °C

2.1: t-BuOK / tetrahydrofuran / 0.5 h / 20 °C

2.2: 56 percent / tetrahydrofuran; benzene / 1.5 h / Heating

3.1: 65 percent / Grubbs' second-generation catalyst / CH₂Cl₂ / 1 h / Heating

4.1: 59 percent / H₂ / Pd/C / ethanol / 16 h / 20 °C

With potassium tert-butylate; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/jm060486f

Reference yield:

: 918423-37-7
(2R,4R,5R)-2-allyl-4-(3-benzyloxy-phenyl)-4,5-dimethyl-piperidin-1-ol

: 918423-47-9
(3S,7R,8R,9aR)-8-(3-hydroxyphenyl)-7,8-dimethyl-3-phenyl-hexahydro-1H-quinolizin-4(6H)-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / Zn; AcOH / H₂O / 3 h / 20 °C / sonication

2.1: 74 percent / N,N-diisopropylethylamine; O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium*BF₄ / acetonitrile / 16 h / 20 °C

3.1: t-BuOK / tetrahydrofuran / 0.5 h / 20 °C

3.2: 56 percent / tetrahydrofuran; benzene / 1.5 h / Heating

4.1: 65 percent / Grubbs' second-generation catalyst / CH₂Cl₂ / 1 h / Heating

5.1: 59 percent / H₂ / Pd/C / ethanol / 16 h / 20 °C

With potassium tert-butylate; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jm060486f