(R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol

Base Information

• Chemical Name: (R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol
• CAS No.: 137171-66-5
• Molecular Formula: C₂₅H₂₉N₃O₃Se
• Molecular Weight: 498.484
• Mol file: 137171-66-5.mol

Synonyms:(R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol

Chemical Property of (R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol

There total 15 articles about (R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol 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: 80.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + (R)-(2S,12bS)-2-(1,2,3,4,6,7,12,12b-Octahydro-indolo[2,3-a]quinolizin-2-yl)-butane-1,4-diol (137171-65-4) → (R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol (137171-66-5)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; for 4h; Heating;

DOI:10.1016/0040-4039(91)80018-2

Reference yield: 39.2%

(R)-(2S,12bS)-2-(1,2,3,4,6,7,12,12b-Octahydro-indolo[2,3-a]quinolizin-2-yl)-butane-1,4-diol (74447-17-9,137171-65-4,137172-75-9) → (R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol (74447-18-0,137171-66-5)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/ja00532a061

Reference yield:

tryptamine (61-54-1) → (R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol (74447-18-0,137171-66-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) ethyl chloroformate, triethylamine / 1.) CH₂Cl₂, room temperature, 4 h, 2.) room temperature

2: 36.8 percent / methyl iodide / acetonitrile; H₂O / 48 h / Ambient temperature

3: 92.5 percent / LiAlH₄ / tetrahydrofuran / 3.5 h / Heating

4: 39.2 percent / tri-n-butylphosphine / tetrahydrofuran / 2 h / Ambient temperature

With lithium aluminium tetrahydride; tributylphosphine; chloroformic acid ethyl ester; triethylamine; methyl iodide; In tetrahydrofuran; water; acetonitrile;

DOI:10.1021/ja00532a061

upstream raw materials:

ortho-nitrophenyl selenocyanate

(R)-(2S,12bS)-2-(1,2,3,4,6,7,12,12b-Octahydro-indolo[2,3-a]quinolizin-2-yl)-butane-1,4-diol

<6S,4R(1'S)>-6-hydroxy-4-<1'-(1',2'-dihydroxyethyl)>-N-tryptophyl-2-piperidone-2'-6-anhydro

(1S,5R)-8-[2-(1H-Indol-3-yl)-ethyl]-2-oxa-8-aza-bicyclo[3.3.1]nonane-4,7-dione

Downstream raw materials:

(+/-)-antirhine

antirhine