(2S,12bS)-2-((E)-1-Hydroxymethyl-propenyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizine-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,12bS)-2-((E)-1-Hydroxymethyl-propenyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizine-3-carboxylic acid methyl ester
• CAS No.: 93894-89-4
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.433
• Mol file: 93894-89-4.mol

Synonyms:

Chemical Property of (2S,12bS)-2-((E)-1-Hydroxymethyl-propenyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizine-3-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,12bS)-2-((E)-1-Hydroxymethyl-propenyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizine-3-carboxylic acid methyl ester

There total 16 articles about (2S,12bS)-2-((E)-1-Hydroxymethyl-propenyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizine-3-carboxylic acid 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: 81.5%

ethyl vallesiachotamate (93862-67-0,93862-68-1) → dihydrovallesiachotamine (5523-49-9,34384-66-2,93862-69-2,93894-89-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 5 ℃;

Reference yield: 78.0%

Methyl <12bS-(2α,12bα)>-1,2,6,7,12,12b-hexahydro-2-<(E/Z)-1-(methoxycarbonyl)prop-1-enyl>indolo<2,3-a>quinolizine-3-carboxylate (114184-86-0,136029-92-0,136085-12-6) → Methyl <12bS-(2α,12bα)>-2-<(E/Z)-1,2,6,7,12,12b-hexahydro-1-(hydroxymethyl)prop-1-enyl>indolo<2,3-a>quinolizine-3-carboxylate (5523-49-9,34384-66-2,93862-69-2,93894-89-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 2h;

Reference yield:

3-methoxycarbonyl-1-[2-(3-indolyl)ethyl]pyridinium bromide (4695-86-7) → dihydrovallesiachotamine (5523-49-9,34384-66-2,93862-69-2,93894-89-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) lithium diisopropylamide / 1.) THF, -50 to 0 deg C,

2: 1.) lithium diisopropylamide / 1.) THF, -40 deg C, 30 min, 2.) -40 to -20 deg C, 2 h

3: 81.5 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C

With lithium aluminium tetrahydride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo00245a027

upstream raw materials:

Methyl <12bS-(2α,12bα)>-1,2,6,7,12,12b-hexahydro-2-<(E/Z)-1-(methoxycarbonyl)prop-1-enyl>indolo<2,3-a>quinolizine-3-carboxylate

N-<β-Indolyl-3-ethyl>-3-t-butyloxycarbonylpyridiniumbromid

tert-Butyl <12bS-(2α,12bα)>-1,2,6,7,12,12b-hexahydro-2-<(E/Z)-1-(methoxycarbonyl)prop-1-enyl>indolo<2,3-a>quinolizine-3-carboxylate

tert-Butyl <12bS-(2α,12bα)>-1,2,6,7,12,12b-hexahydro-2-<(1R,2R)-2-hydroxy-1-(methoxycarbonyl)propyl>indolo<2,3-a>quinolizine-3-carboxylate

Downstream raw materials:

vallesiachotamine

(E)-vallesiachotamine

isovallesiachotamine

tetrahydrovallesiachotamine