1,2,3,5,6,10b-Hexahydro-8,9-diMethoxypyrrolo[2,1-a]isoquinoline

Base Information

• Chemical Name: 1,2,3,5,6,10b-Hexahydro-8,9-diMethoxypyrrolo[2,1-a]isoquinoline
• CAS No.: 15889-93-7
• Molecular Formula: C14H19NO2
• Molecular Weight: 450.33700
• Mol file: 15889-93-7.mol

Synonyms:8,0-dimethoxy-1,2,3,5,6,10b;(+/-)-8,9-dimethoxy-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline;hexahydropyrrolo<2,1-a>isoquinoline;1,2,3,5,6,10b-Hexahydro-8,9-dimethoxypyrrolo[2,1-a]isoquinoline;Crispine A;

Chemical Property of 1,2,3,5,6,10b-Hexahydro-8,9-diMethoxypyrrolo[2,1-a]isoquinoline

Chemical Property:

• Melting Point: 87-88 °C
• Boiling Point: 110-120 °C(Press: 0.02 Torr)
• PKA: 8.31±0.20(Predicted)
• PSA: 77.99000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 5.94770

Purity/Quality:

CrispineA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Crispine A is a tricyclic indolizidine alkaloid as potent α2-adrenoceptor antagonist.

Technology Process of 1,2,3,5,6,10b-Hexahydro-8,9-diMethoxypyrrolo[2,1-a]isoquinoline

There total 64 articles about 1,2,3,5,6,10b-Hexahydro-8,9-diMethoxypyrrolo[2,1-a]isoquinoline 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: 95.0%

1-(3-hydroxypropyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (148204-28-8) → (+/-)-crispine A (15889-93-7)

Guidance literature:

1-(3-hydroxypropyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; With thionyl chloride; In dichloromethane; at 40 ℃;

In 1,2-dimethoxyethane; water; at 40 ℃; for 3h; Further stages.;

DOI:10.1021/jo701877h

Reference yield: 94.0%

8,9-bis(methyloxy)-2,3,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(1H)-one (104058-44-8) → (+/-)-crispine A (15889-93-7)

Guidance literature:

With lithium aluminium tetrahydride; triethylamine hydrochloride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol900702t

Reference yield: 91.0%

(+/-)-8,9-dimethoxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one (33545-52-7) → (+/-)-crispine A (15889-93-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;

DOI:10.3987/COM-88-4647

upstream raw materials:

8,9-dimethoxy-2,3,5,6-tetrahydro-1H-pyrrolo<2,1-a>isoquinolinium chloride

N-<2-(3,4-dimethoxyphenyl)ethyl>proline

N-chloro-N-cyclobutyl-3,4-dimethoxyphenethylamine

2-(3-Iodo-propyl)-6,7-dimethoxy-3,4-dihydro-isoquinolinium; iodide

Downstream raw materials:

C₁₀H₁₅OPS*C₁₄H₁₉NO₂

C₁₀H₁₅OPS*C₁₄H₁₉NO₂

Refernces

• 1、 Meyer, Nino,Opatz, Till. "One-pot synthesis of (±)-crispine A and its C-ring-substituted analogs". . p. 3997 - 4002. Retrieved 2006.
• 2、 Saha, Sanjay,Venkata Ramana Reddy, Ch.,Patro, Balaram. "Facile two-step synthesis of crispine A and harmicine by cyclopropylimine rearrangement". . p. 4014 - 4016. Retrieved 2011.
• 3、 He, Qian,Ye, Jian-Liang,Xu, Fang-Fang,Geng, Hui,Chen, Ting-Ting,Chen, Hang,Huang, Pei-Qiang. "Tf2O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides". . . Retrieved 2021/09/28.
• 4、 Drici, Wassila,Fayssal, Sandra Abi,Lazouni, Imane,Pérard-Viret, Jo?lle,Souquet, Florence,Thueillon, Sébastien. "N -Acyliminium Ion Chemistry: Improving the Access to Unsaturated γ-Lactams and Their N -α-Methoxylated Derivatives: Application to an Expeditive Synthesis of (±)-Crispine A". . p. 2970 - 2978. Retrieved 2020/10/18.