Rotundine

Base Information

• Chemical Name: Rotundine
• CAS No.: 6808-63-5
• Molecular Formula: C19H21NO4
• Molecular Weight: 327.37
• Mol file: 6808-63-5.mol

Synonyms:(-)-Bisnorargemonine;Bisnorargemonine;

Chemical Property of Rotundine

Chemical Property:

• PSA: 62.16000
• LogP: 2.87930

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Rotundine

There total 5 articles about Rotundine 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: 32.0%

(-)-N-Carbethoxy-N-norbisnorargemonine (72259-06-4) → bisnorargemonine (6808-63-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 18h; Heating;

DOI:10.1021/jo01292a009

Reference yield:

(+)-3,4-Dehydro-N-carbethoxy-N-norreticuline (72259-05-3) → bisnorargemonine (6808-63-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / CH₃SO₃H / acetonitrile / 1.5 h / 25 °C

2: 32 percent / LAH / tetrahydrofuran / 18 h / Heating

With lithium aluminium tetrahydride; methanesulfonic acid; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo01292a009

Reference yield:

(+)-4-Methoxy-N-carbethoxy-N-norreticuline (72264-53-0) → bisnorargemonine (6808-63-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / 1 h / 190 - 200 °C / 200 Torr

2: 81 percent / CH₃SO₃H / acetonitrile / 1.5 h / 25 °C

3: 32 percent / LAH / tetrahydrofuran / 18 h / Heating

With lithium aluminium tetrahydride; methanesulfonic acid; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo01292a009

upstream raw materials:

(-)-N-Carbethoxy-N-norbisnorargemonine

(+)-3,4-Dehydro-N-carbethoxy-N-norreticuline

(+)-4-Methoxy-N-carbethoxy-N-norreticuline

(+)-N-carbethoxy-N-norreticuline

Downstream raw materials:

(-)-argemonine

Refernces