(2R,3R,11bR)-10-methoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine-2,9-diol

Base Information

• Chemical Name: (2R,3R,11bR)-10-methoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine-2,9-diol
• CAS No.: 1065193-59-0
• Molecular Formula: C₁₈H₂₇NO₃
• Molecular Weight: 305.417
• NSC Number: 750374
• UNII: P3M4TU3OJF,5MCJ8D6Q25
• Wikidata: Q27216244
• Mol file: 1065193-59-0.mol

Synonyms:(+)-9-deMe-DTBZ;1065193-59-0;(+/-)-9-deMe-DTBZ;956903-21-2;P3M4TU3OJF;NSC-750374;(+)-9-O-Desmethyl-a-dihydrotetrabenazine;5MCJ8D6Q25;SD-971;(2R,3R,11bR)-10-methoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine-2,9-diol;5220-98-4;(2R,3R,11bR)-1,3,4,6,7,11b-Hexahydro-10-methoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizine-2,9-diol;2H-Benzo(a)quinolizine-2,9-diol, 1,3,4,6,7,11b-hexahydro-10-methoxy-3-(2-methylpropyl)-, (2R,3R,11bR)-;2H-Benzo(a)quinolizine-2,9-diol, 1,3,4,6,7,11b-hexahydro-10-methoxy-3-(2-methylpropyl)-, (2R,3R,11bR)-rel-;2H-Benzo[a]quinolizine-2,9-diol, 1,3,4,6,7,11b-hexahydro-10-methoxy-3-(2-methylpropyl)-, (2R,3R,11bR)-rel-;Rel-(2R,3R,11bR)-1,3,4,6,7,11b-hexahydro-10-methoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizine-2,9-diol;UNII-P3M4TU3OJF;9-o-Desmethyl-alpha-htbz;UNII-5MCJ8D6Q25;(+)-9-O-DESMETHYL-ALPHA-DIHYDROTETRABENAZINE;(+)-9-o-Desmethyl-alpha-htbz;SCHEMBL13401107;CHEBI:125633;(+/-)-9-o-Desmethyl-alpha-htbz;9-O-DESMETHYL-.ALPHA.-HTBZ;NSC750374;9-o-Desmethyl-alpha-dihydrotetrabenazine;(+)-9-O-DESMETHYL-.ALPHA.-HTBZ;(+/-)-9-O-DESMETHYL-.ALPHA.-HTBZ;9-O-DESMETHYL-.ALPHA.-DIHYDROTETRABENAZINE;BRD-K76941385-001-01-2;Q27216244;(+)-9-O-DESMETHYL-.ALPHA.-DIHYDROTETRABENAZINE

Chemical Property of (2R,3R,11bR)-10-methoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine-2,9-diol

Chemical Property:

• Melting Point: >201°C (dec.)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly, Sonicated)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 305.19909372
• Heavy Atom Count: 22
• Complexity: 375

Purity/Quality:

97% ^*data from raw suppliers

(+)-9-deMe-DTBZ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CC1CN2CCC3=CC(=C(C=C3C2CC1O)OC)O
• Isomeric SMILES: CC(C)C[C@@H]1CN2CCC3=CC(=C(C=C3[C@H]2C[C@H]1O)OC)O
• Uses: (+)-9-deMe-DTBZ is a desmethyl derivative of Tetrabenzine (T284000), a dopamine depleting agent. An antidyskinetic; antipsychotic.

Technology Process of (2R,3R,11bR)-10-methoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine-2,9-diol

There total 13 articles about (2R,3R,11bR)-10-methoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine-2,9-diol 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: 96.0%

(2R,3R,11bR)-9-(benzyloxy)-3-isobutyl-10-methoxy-2,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol (1141448-87-4) → (2R,3R,11bR)-3-isobutyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-2,9-diol (1065193-59-0,1065193-41-0,956903-21-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; ethanol; at 20 ℃;

DOI:10.1016/j.nucmedbio.2019.07.002

Reference yield:

isovanillin (621-59-0) → (2R,3R,11bR)-3-isobutyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-2,9-diol (1065193-59-0,1065193-41-0,956903-21-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium carbonate / acetonitrile / 3 h / 20 °C / Reflux

2.1: ammonium acetate; acetic acid / 7.5 h / 93 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / -10 °C / Reflux

4.1: 55 °C

5.1: trichlorophosphate / dichloromethane / 25 °C

6.1: methanol / 31 h / 20 °C / Reflux

7.1: sodium tetrahydroborate / ethanol / 0.3 h / 25 °C

8.1: methanol / 0.5 h / 20 - 45 °C

9.1: acetone

9.2: pH 10

10.1: 5%-palladium/activated carbon; hydrogen / ethanol / 48 h / 25 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; 5%-palladium/activated carbon; ammonium acetate; hydrogen; potassium carbonate; acetic acid; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; acetonitrile; 2.1: |Henry Nitro Aldol Condensation / 5.1: |Bischler-Napieralski Reaction;

DOI:10.1080/00397911.2019.1663539

Reference yield:

3-benzyloxy-4-methoxybenzaldehyde (6346-05-0) → (2R,3R,11bR)-3-isobutyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-2,9-diol (1065193-59-0,1065193-41-0,956903-21-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: ammonium acetate; acetic acid / 7.5 h / 93 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / -10 °C / Reflux

3.1: acetic acid; trifluoroacetic acid / 18 h / 90 °C

4.1: methanol / 31 h / 20 °C / Reflux

5.1: sodium tetrahydroborate / ethanol / 0.3 h / 25 °C

6.1: methanol / 0.5 h / 20 - 45 °C

7.1: acetone

7.2: pH 10

8.1: 5%-palladium/activated carbon; hydrogen / ethanol / 48 h / 25 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; 5%-palladium/activated carbon; ammonium acetate; hydrogen; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; acetone; 1.1: |Henry Nitro Aldol Condensation / 3.1: |Pictet-Spengler Synthesis;

DOI:10.1080/00397911.2019.1663539

upstream raw materials:

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

9-(benzyloxy)-3-isobutyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one

5-Methyl-2-hexanone

isovanillin