Ochrobirine

Base Information

• Chemical Name: Ochrobirine
• CAS No.: 24181-64-4
• Molecular Formula: C₂₀H₁₉NO₆
• Molecular Weight: 369.374
• Mol file: 24181-64-4.mol

Synonyms:Ochrobirine(8CI); Spiro[1,3-dioxolo[4,5-g]isoquinoline-5(6H),7'-[7H]indeno[4,5-d][1,3]dioxole]-6',8'-diol,6',7,8,8'-tetrahydro-6-methyl-, [6'S-(6'a,7'b,8'b)]-; [6'S-(6'a,7'b,8'b)]-6',7,8,8'-Tetrahydro-6-methylspiro[1,3-dioxolo[4,5-g]isoquinoline-5(6H),7'-[7H]indeno[4,5-d][1,3]dioxole]-6',8'-diol;d-Ochrobirine

Chemical Property of Ochrobirine

Chemical Property:

• Melting Point: 198°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: A Corydalis alkaloid, this base is found in C. lutea (L.) D. C., C. ochroleuca Koch and C. sibirica Pers. It forms colourless crystals from MeOH with I mole of solvent, m.p. l38-9°C and has [α] 21 + 35.9° (CHCI3). It yields a crystalline acetate, m.p. 177°C and on treatment with Zn-amalgam is converted into an isomeric base with m.p. 238°C. The structure of the alkaloid, deduced from chemical and physical evidence has been confirmed by the synthesis of the optically active form.

Technology Process of Ochrobirine

There total 40 articles about Ochrobirine 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: 91.0%

(+/-)-sibiricine (24181-66-6,31456-80-1,64397-09-7,64397-10-0) → (+/-)-sewercinine (24181-64-4,33805-02-6,68736-95-8,76231-96-4,99265-30-2,126187-21-1)

Guidance literature:

With sodium tetrahydroborate; In methanol;

Reference yield: 73.0%

7,8,6',8'-tetrahydro-6H-(7'rN)-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6't,8'c-diol (84229-91-4) + methyl iodide (74-88-4) → (+/-)-Ochrobirin (24181-64-4,33805-02-6,68736-95-8,76231-96-4,99265-30-2,126187-21-1)

Guidance literature:

In tetrahydrofuran; Ambient temperature;

Reference yield:

6-acetyl-6H-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-dione (38854-62-5) → (+/-)-Ochrobirin (24181-64-4,33805-02-6,68736-95-8,76231-96-4,99265-30-2,126187-21-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Adams catalyst / acetic acid / 1810.02 Torr

2: aq. HCl / ethanol / Heating

3: HCO₂H

4: NaBH₄ / ethanol / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; formic acid; hydrogen; platinum(IV) oxide; In ethanol; acetic acid;

DOI:10.1139/v72-481

upstream raw materials:

6-methyl-7,8-dihydro-6H-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-dione

7,8-dihydro-6H-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-dione

6-acetyl-6H-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-dione

6-acetyl-7,8-dihydro-6H-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-dione

Refernces

• 1、 Hanaoka, Miyoji,Sakurai, Shun-ichiro,Ohshima, Takeshi,Yasuda, Shingo,Mukai, Chisato. "TRANSFORMATION OF PROTOBERBERINES INTO SPIROBENZYLISOQUINOLINES. STEREOSELECTIVE CONVERSION OF COPTISINE INTO (+/-)-OCHROBIRINE". . p. 3446 - 3449. Retrieved 2007/10/02.