(2S,3S,11bR)-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-ethanol

Base Information

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

Synonyms:(2S,3S,11bR)-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-ethanol

Chemical Property of (2S,3S,11bR)-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

There total 4 articles about (2S,3S,11bR)-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-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: 85.0%

(2S,3S,11bR)-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-acetic acid ethyl ester (109009-03-2) → (2S,3S,11bR)-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-ethanol (109009-04-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 4h; Heating;

DOI:10.1248/cpb.34.669

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:

(2S,3S)-8-Benzyloxy-2-ethoxycarbonylmethyl-3-ethyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-pyrido[2,1-a]isoquinolinylium; chloride (56774-71-1,57130-33-3,57130-34-4,73136-35-3) → (2S,3S,11bR)-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-ethanol (109009-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Adams catalyst / ethanol / 0.67 h / 22 °C

2: 85 percent / LiAlH₄ / diethyl ether / 4 h / Heating

With lithium aluminium tetrahydride; hydrogen; platinum(IV) oxide; In diethyl ether; ethanol;

DOI:10.1248/cpb.34.669

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

(2S,3S,11bR)-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-acetic acid ethyl ester

(2S,3S)-8-Benzyloxy-2-ethoxycarbonylmethyl-3-ethyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-pyrido[2,1-a]isoquinolinylium; chloride

Downstream raw materials:

(+/-)-ankorine

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