(-)-Vallesamidine

Base Information

• Chemical Name: (-)-Vallesamidine
• CAS No.: 19637-77-5
• Molecular Formula: C20H28N2
• Molecular Weight: 296.45
• Mol file: 19637-77-5.mol

Synonyms:(5aR,10aS,12aR,12bR)-12a-Ethyl-10-methyl-2,3,4,5,5a,10,11,12,12a,12b-decahydro-1H-3a,10-diaza-indeno[1,7-ma]fluorene;Vallesamidin;

Chemical Property of (-)-Vallesamidine

Chemical Property:

• PSA: 6.48000
• LogP: 4.02000

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: An alkaloid found in species of Vallesia, particularly V. dichotoma and V. glabra. The structure and absolute configuration have been determined by X-ray diffraction analysis of the methiodide which crystallizes in space group P2 1 and has a = 11.977, b = 12.009 and c = 9.4224 A.

Technology Process of (-)-Vallesamidine

There total 25 articles about (-)-Vallesamidine 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: 91.0%

C20H26N2O → (-)-vallesamidine (19637-77-5)

Guidance literature:

With carbonylhydridetris(triphenylphosphine)rhodium(I); phenylsilane; In tetrahydrofuran; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.chempr.2017.04.007

Reference yield: 82.0%

(6aR,11aS,13aS,13bR)-13a-ethyl-1,2,5,6,6a,11,12,13,13a,13b-decahydro-11-methyl-3H-cyclopenta[ij]-indolo[2,3-a]quinolizin-3-one (442632-42-0) → (-)-vallesamidine (19637-77-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 70 ℃; for 0.5h;

DOI:10.1016/S0040-4039(02)00256-3

Reference yield:

(3R)-3-ethyldihydro-3-(2-propenyl)-2(3H)-furanone (442632-27-1) → (-)-vallesamidine (19637-77-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: diisobutylaluminum hydride / diethyl ether / 1 h / -78 °C

1.2: 84 percent / p-toluenesulfonic acid / methanol / 0.67 h / Heating

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran; hexane / 20 °C

2.2: 87 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; hexane / 0 - 20 °C

3.1: sulfur trioxide pyridine complex; methyl sulfoxide; triethylamine / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 95 percent / 2-methyl-2-butene; sodium dihydrogenphosphate dihydrate; sodium chlorite / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

5.1: 43 percent / 144 h / 125 °C

6.1: 72 percent / aq. NaOH / methanol / 1 h / 20 °C

7.1: 92 percent / 4-(dimethylamino)pyridine; pyridine / 2 h / 0 °C

8.1: 68 percent / sodium borohydride / ethanol / 3 h / 0 - 20 °C

9.1: sodium cyanoborohydride / acetonitrile / 0.17 h / 20 °C

9.2: 87 percent / acetic acid / acetonitrile / 1 h / 20 °C

10.1: 82 percent / lithium aluminum hydride / tetrahydrofuran / 0.5 h / 70 °C

With pyridine; dmap; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; sulfur trioxide pyridine complex; diisobutylaluminium hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/j.tet.2004.02.015

upstream raw materials:

(6aR,11aS,13aS,13bR)-13a-ethyl-1,2,5,6,6a,11,12,13,13a,13b-decahydro-11-methyl-3H-cyclopenta[ij]-indolo[2,3-a]quinolizin-3-one

(3R)-3-ethyldihydro-3-(2-propenyl)-2(3H)-furanone

(3R)-3-ethyltetrahydro-2-methoxy-3-(2-propenyl)furan

(3R)-3-ethyldihydro-5-hydroxy-3-(2-propenyl)-2(3H)-furanone

Refernces

• 1、 Wang, Xiaobei,Xia, Dongliang,Qin, Wenfang,Zhou, Ruijie,Zhou, Xiaohan,Zhou, Qilong,Liu, Wentao,Dai, Xiang,Wang, Huijing,Wang, Shuqing,Tan, Ling,Zhang, Dan,Song, Hao,Liu, Xiao-Yu,Qin, Yong. "A Radical Cascade Enabling Collective Syntheses of Natural Products". . p. 803 - 816. Retrieved 2017/06/13.