(3S,16R,14R)-14-deoxyvincamine

Base Information

• Chemical Name: (3S,16R,14R)-14-deoxyvincamine
• CAS No.: 105500-11-6
• Molecular Formula: C₂₁H₂₆N₂O₂
• Molecular Weight: 338.45
• Mol file: 105500-11-6.mol

Synonyms:

Chemical Property of (3S,16R,14R)-14-deoxyvincamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,16R,14R)-14-deoxyvincamine

There total 21 articles about (3S,16R,14R)-14-deoxyvincamine 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: 27.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (+/-)-eburnane-16β-carbonitrile (59639-59-7,61826-71-9,61848-76-8,62474-77-5,70614-21-0,123806-79-1,123806-80-4,123806-81-5) → (10R,11aR,11bR)-11a-Ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid amide (59656-84-7,70614-84-5,71075-45-1,123806-82-6,123806-83-7,123806-84-8) + deoxyvincamine (21019-23-8,21019-24-9,57130-30-0,59684-93-4,68779-69-1,68779-71-5,70614-18-5,80735-18-8,96245-03-3,96245-04-4,105500-11-6,105500-21-8,105561-05-5,105561-07-7)

Guidance literature:

With hydrogenchloride; Yield given. Multistep reaction; 1. reflux, 8 h; 2. ether;

Reference yield:

1-propyl-4,9-dihydro-3H-pyrido<3,4-b>indole (68796-67-8) → deoxyvincamine (21019-23-8,21019-24-9,57130-30-0,59684-93-4,68779-69-1,68779-71-5,70614-18-5,80735-18-8,96245-03-3,96245-04-4,105500-11-6,105500-21-8,105561-05-5,105561-07-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / 1.) i-Pr₂NEt, 2.) LiClO₄ / acetonitrile / 8 h / Heating

2: 5.4 g / 1.) i-Pr₂NEt / acetonitrile; H₂O / 3 h / Heating

3: 88 percent / DMSO, DCC, H₃PO₄ / 3 h / Ambient temperature

4: 2.58 g / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 40 °C

5: 84 percent / t-BuOK / benzene / 2 h / Ambient temperature

6: H₂ / 10percent Pd/C / methanol / 1 h

With phosphoric acid; potassium tert-butylate; hydrogen; lithium perchlorate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; water; acetonitrile; tert-butyl alcohol; benzene;

Reference yield:

1-ethyl-2,3,4,6,7,12-hexahydro-indolo(2,3-a)quinolizinium perchlorate (55390-29-9) → deoxyvincamine (21019-23-8,21019-24-9,57130-30-0,59684-93-4,68779-69-1,68779-71-5,70614-18-5,80735-18-8,96245-03-3,96245-04-4,105500-11-6,105500-21-8,105561-05-5,105561-07-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 5.4 g / 1.) i-Pr₂NEt / acetonitrile; H₂O / 3 h / Heating

2: 88 percent / DMSO, DCC, H₃PO₄ / 3 h / Ambient temperature

3: 2.58 g / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 40 °C

4: 84 percent / t-BuOK / benzene / 2 h / Ambient temperature

5: H₂ / 10percent Pd/C / methanol / 1 h

With phosphoric acid; potassium tert-butylate; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; water; acetonitrile; tert-butyl alcohol; benzene;

upstream raw materials:

diazomethane

(10S,11aS,11bR)-11a-Ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carbonitrile

(10R,11aS,11bR)-11a-Ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carbonitrile

(+/-)-eburnane-16β-carbonitrile

Downstream raw materials:

(-)-3S,16R,14R-14,15-dihydro-14-hydroxymethyl-eburnamenine

Refernces

• 1、 Danieli, Bruno,Lesma, Giordano,Palmisano, Giovanni. "A NEW APPROACH TO (+/-)-APOVINCAMINE". . p. 257 - 268. Retrieved 2007/10/02.