(2S,3R,11bR)-3-Isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol

Base Information

• Chemical Name: (2S,3R,11bR)-3-Isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol
• CAS No.: 113627-25-1
• Molecular Formula: C₁₉H₂₉NO₃
• Molecular Weight: 319.444
• UNII: R2FU181UOU,UV9ZV84BDS
• ChEMBL ID: CHEMBL1770801
• DSSTox Substance ID: DTXSID90561897
• Nikkaji Number: J3.262.239I
• Mol file: 113627-25-1.mol

Synonyms:924854-60-4;(2S,3R,11bR)-3-Isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol;Tetrabenazine Metabolite;(+)-beta-Dihydrotetrabenazine;UV9ZV84BDS;Tetrabenazine metabolite M5;R2FU181UOU;CHEMBL1770801;(2S,3R,11bR)-Dihydrotetrabenazine;SD-947;(2S,3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-ol;Dihydrotetrabenazine, (2S,3R,11bR)-;(2S,3R,11BR)-9,10-dimethoxy-3-(2-methylpropyl)-1H,2h,3h,4h,6h,7h,11bH-pyrido[2,1-a]isoquinolin-2-ol;(2S,3R,11bR)-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizin-2-ol;2H-Benzo(a)quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (2R,3S,11bS)-rel-;2H-Benzo(a)quinolizin-2-ol, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (2S,3R,11bR)-;Rel-(2R,3S,11bS)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizin-2-ol;beta-Htbz;WEQLWGNDNRARGE-OIISXLGYSA-N;(+)-beta-Htbn;(+/-)-beta-Htbz;beta-Dihydrotetrabenazine;UNII-UV9ZV84BDS;.BETA.-HTBZ;UNII-R2FU181UOU;(2)-Dihydrotetrabenazine-D7;(+)-.BETA.-HTBN;SCHEMBL2755525;DTXSID90561897;(+/-)-.BETA.-HTBZ;.BETA.-DIHYDROTETRABENAZINE;(2R,3S,11bS)-3-Isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol;HY-G0025;ZLB85460;BDBM50342820;AKOS015852376;(-)--Dihydrotetrabenazine;(-)--HTBZ;(+)-.BETA.-DIHYDROTETRABENAZINE;AS-53398;CS-0054559;P16428;(2S,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol;(2S,3R,11bR)-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11bhexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol;(2S,3R,11bR)-9,10-Dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol

Chemical Property of (2S,3R,11bR)-3-Isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 156-158°C (dec.)
• Boiling Point: 457.82°C at 760 mmHg
• PKA: 14.75±0.40(Predicted)
• Flash Point: 230.682°C
• PSA: 41.93000
• Density: 1.13g/cm³
• LogP: 2.96780
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 319.21474379
• Heavy Atom Count: 23
• Complexity: 389

Purity/Quality:

98.5% ^*data from raw suppliers

cis(2,3)-DihydroTetrabenazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1CN2CCC3=CC(=C(C=C3C2CC1O)OC)OC
• Isomeric SMILES: CC(C)C[C@@H]1CN2CCC3=CC(=C(C=C3[C@H]2C[C@@H]1O)OC)OC
• Uses: A metabolite of Tetrabenazine in vivo, which is likely the active pharmacological agent. The cis isomer of Dihydrotetrabenazine is used for the treatment of hyperkinetic movement disorders. cis (2,3)-Dihydro Tetrabenazine is a metabolite of Tetrabenazine in vivo, which is likely the active pharmacological agent. The cis izomer of Dihydrotetrabenazine is used for the treatment of hyperkinetic movement disorders.

Technology Process of (2S,3R,11bR)-3-Isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-ol

There total 17 articles about (2S,3R,11bR)-3-Isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-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%

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one (58-46-8,1381929-92-5) → 2α-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine (3466-75-9,7744-53-8,7744-54-9,85081-18-1,113627-25-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol202792q

Reference yield: 80.0%

tetrabenazine (718635-93-9,1381929-92-5) → 2β-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine (3466-75-9,7744-53-8,7744-54-9,85081-18-1,113627-25-1)

Guidance literature:

With L-selectride; In tetrahydrofuran; ethanol; at 0 - 20 ℃; for 1h; Product distribution / selectivity;

Reference yield: 67.0%

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one (58-46-8,1381929-92-5) → 2β-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine (3466-75-9,7744-53-8,7744-54-9,85081-18-1,113627-25-1)

Guidance literature:

With L-Selectride; In tetrahydrofuran; ethanol; at 0 - 20 ℃; for 0.5 - 6.5h; Product distribution / selectivity;

upstream raw materials:

(3R^*,11bR^*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl-4-methylbenzenesulfonate

6,7-dimethoxy-2-(4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl)-1,2,3,4-tetrahydroisoquinoline

methyl 4-methyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentanoate

Downstream raw materials:

C₂₉H₃₆F₃NO₅

C₂₉H₃₆F₃NO₅

C₂₉H₃₆F₃NO₅

C₂₉H₃₆F₃NO₅