(4aR,6S,8aS)-4a-(3,4-Dimethoxy-phenyl)-octahydro-isoquinoline-2,6-dicarboxylic acid 2-methyl ester

Base Information

Chemical Name:(4aR,6S,8aS)-4a-(3,4-Dimethoxy-phenyl)-octahydro-isoquinoline-2,6-dicarboxylic acid 2-methyl ester
CAS No.:99809-87-7
Molecular Formula:C₂₀H₂₇NO₆
Molecular Weight:377.437
Hs Code.:

Synonyms:(4aR,6S,8aS)-4a-(3,4-Dimethoxy-phenyl)-octahydro-isoquinoline-2,6-dicarboxylic acid 2-methyl ester

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Chemical Property of (4aR,6S,8aS)-4a-(3,4-Dimethoxy-phenyl)-octahydro-isoquinoline-2,6-dicarboxylic acid 2-methyl ester

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Technology Process of (4aR,6S,8aS)-4a-(3,4-Dimethoxy-phenyl)-octahydro-isoquinoline-2,6-dicarboxylic acid 2-methyl ester

There total 13 articles about (4aR,6S,8aS)-4a-(3,4-Dimethoxy-phenyl)-octahydro-isoquinoline-2,6-dicarboxylic acid 2-methyl ester 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: 73.6%

: 64-18-6
formic acid

: 97580-39-7
{2-[1-(3,4-Dimethoxy-phenyl)-vinyl]-hex-5-enyl}-hydroxymethyl-carbamic acid methyl ester

: 99809-87-7
(4aR,6S,8aS)-4a-(3,4-Dimethoxy-phenyl)-octahydro-isoquinoline-2,6-dicarboxylic acid 2-methyl ester

Guidance literature:: for 2h; Ambient temperature;
DOI:10.1021/jo00354a035

Reference yield: 73.6%

: 64-18-6
formic acid

: 97580-39-7
{2-[1-(3,4-Dimethoxy-phenyl)-vinyl]-hex-5-enyl}-hydroxymethyl-carbamic acid methyl ester

: 97579-68-5,99809-87-7
(4aS,6R,8aR)-4a-(3,4-Dimethoxy-phenyl)-6-formyloxy-octahydro-isoquinoline-2-carboxylic acid methyl ester

Guidance literature:: DOI:10.1016/S0040-4039(00)98544-7

Reference yield:

: 67409-10-3
ethyl (E)-3-(3,4-dimethoxyphenyl)-2-butenoate

: 99809-87-7
(4aR,6S,8aS)-4a-(3,4-Dimethoxy-phenyl)-octahydro-isoquinoline-2,6-dicarboxylic acid 2-methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) n-BuLi, diisopropylamine / 1.) hexane, THF, -78 deg C, 0.5 h, 2.) hexane, THF, RT, 1 h

2: 90 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

3: 73 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

4: hydrazine hydrate / ethanol / 3 h / Heating

5: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

6: 56 percent / Cs₂CO₃ / tetrahydrofuran / 15 h / Ambient temperature

7: 73.6 percent / 2 h / Ambient temperature

With lithium aluminium tetrahydride; n-butyllithium; di-isopropyl azodicarboxylate; caesium carbonate; hydrazine hydrate; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;
DOI:10.1021/jo00354a035