(+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-ethanol

Base Information

• Chemical Name: (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzo
• Molecular Formula: C₂₆H₃₅NO₄
• Molecular Weight: 425.568

Synonyms:

Chemical Property of (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzo

Chemical Property:

Purity/Quality:

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Useful:

There total 2 articles about (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-ethanol 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:

trans-8-benzyloxy-2-ethoxycarbonylmethyl-3-ethyl-1,2,3,4,6,7-hexahydro-9,10-dimethoxybenzoquinolizinium chloride (73136-35-3) → (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-ethanol (56774-73-3,73136-36-4,109009-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / Adams-catalyst / ethanol / 2 h / 20 °C / 760 Torr

2: 1.) LiAlH₄; 2.) 10percent aq. NaOH / 1.) ether, 1 atm, 30 min; 2.) reflux, water, 4 h

With sodium hydroxide; lithium aluminium tetrahydride; platinum(IV) oxide; In ethanol;

DOI:10.1016/0040-4020(80)80049-4

Reference yield:

ethyl (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-acetate (56774-72-2,57130-35-5,109009-03-2) → (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-ethanol (56774-73-3,73136-36-4,109009-04-3)

Guidance literature:

With sodium hydroxide; lithium aluminium tetrahydride; Yield given. Multistep reaction; 1.) ether, 1 atm, 30 min; 2.) reflux, water, 4 h;

DOI:10.1016/0040-4020(80)80049-4

Reference yield: 98.0%

(+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-ethanol (56774-73-3,73136-36-4,109009-04-3) → (+/-)-ankorine (13849-54-2,56816-22-9,60562-79-0,109527-29-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 0.583333h; under 760 Torr;

DOI:10.1016/0040-4020(80)80049-4

upstream raw materials:

ethyl (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-acetate

trans-8-benzyloxy-2-ethoxycarbonylmethyl-3-ethyl-1,2,3,4,6,7-hexahydro-9,10-dimethoxybenzoquinolizinium chloride

Downstream raw materials:

(+/-)-ankorine

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