(-)-9-deMe-DTBZ

Base Information

• Chemical Name: (-)-9-deMe-DTBZ
• CAS No.: 1065193-41-0
• Molecular Formula: C18H27NO3
• Molecular Weight: 305.41
• Mol file: 1065193-41-0.mol

Synonyms:(-)-9-deMe-DTBZ;(2S,3S,11bS)-1,3,4,6,7,11b-Hexahydro-10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizine-2,9-diol

Chemical Property of (-)-9-deMe-DTBZ

Chemical Property:

• PSA: 52.93000
• LogP: 2.66480

Purity/Quality:

≥95% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (-)-9-deMe-DTBZ is a desmethyl derivative of Tetrabenzine (T284000), a dopamine depleting agent. An antidyskinetic; antipsychotic.

Technology Process of (-)-9-deMe-DTBZ

There total 16 articles about (-)-9-deMe-DTBZ 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: 36.0%

Dihydrotetrabenazine (3466-75-9) → (+/-)-9-O-desmethyldihydrotetrabenazine (5220-98-4,1065193-41-0,956903-21-2)

Guidance literature:

With sodium hydride; 4-hydroxymethyl-3-methoxyphenoxyacetic acid; N-methylaniline; In xylene; at 65 ℃; for 48h;

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

upstream raw materials:

Dihydrotetrabenazine

(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