Isoreserpine

Base Information

• Chemical Name: Isoreserpine
• CAS No.: 482-85-9
• Molecular Formula: C33H40 N2 O9
• Molecular Weight: 608.689
• DSSTox Substance ID: DTXSID50858952
• Nikkaji Number: J125.604A
• Wikidata: Q27164362
• ChEMBL ID: CHEMBL388848
• Mol file: 482-85-9.mol

Synonyms:Isoreserpine;482-85-9;3-Epireserpine;3-Isoreserpine;(-)-Isoreserpine;NSC 80138;20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester) (8CI);Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)-, methyl ester, (16beta,17alpha,18beta,20alpha)-;NSC80138;Spectrum_000004;Spectrum2_001770;Spectrum3_001236;Spectrum5_000924;BSPBio_002712;KBioSS_000344;SPECTRUM300534;methyl dimethoxy-(3,4,5-trimethoxybenzoyl)oxy-[?]carboxylate;DivK1c_000200;SCHEMBL731599;SPBio_001639;CHEMBL388848;BCBcMAP01_000242;CHEBI:92652;HMS500J22;KBio1_000200;KBio2_000344;KBio2_002912;KBio2_005480;KBio3_002212;DTXSID50858952;NINDS_000200;CCG-39604;AKOS040752126;IDI1_000200;SMP1_000292;R0007;EN300-19736137;BRD-K37080523-001-01-0;Q27164362;(1S,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[oxo-(3,4,5-trimethoxyphenyl)methoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid methyl ester;20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester);methyl (1S,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;methyl (1S,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate

Chemical Property of Isoreserpine

Chemical Property:

• Melting Point: 148-155 °C(lit.)
• Boiling Point: 700.1°Cat760mmHg
• PKA: 18.11±0.70(Predicted)
• Flash Point: 377.2°C
• PSA: 117.78000
• Density: 1.32g/cm³
• LogP: 4.10900
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 608.27338086
• Heavy Atom Count: 44
• Complexity: 1000

Purity/Quality:

99% ^*data from raw suppliers

ISORESERPINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
• Isomeric SMILES: CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC

Technology Process of Isoreserpine

There total 88 articles about Isoreserpine 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: 95.0%

3,4,5-Trimethoxybenzoyl chloride (4521-61-3) + (+/-)-methyl reserpate (2901-66-8,16676-49-6,17138-18-0,20686-05-9,20686-09-3,101053-19-4) → (+/-)-3-isoreserpine (50-55-5,482-85-9,1263-58-7,6872-69-1,17138-19-1,17298-47-4,72151-85-0,72173-53-6,75331-15-6)

Guidance literature:

With pyridine; at 20 ℃; for 96h;

DOI:10.1021/ja055744x

Reference yield:

2-(6-methoxy-1H-indol-3-yl)ethan-1-ol (41340-31-2) → Isoreserpin (482-85-9)

Guidance literature:

Multi-step reaction with 8 steps

1: PBr₃

2: 85 percent / K₂CO₃ / methanol / 25 h / Heating

3: 2.) NaBH₄

4: 53 percent

5: 62 percent / 0.3M KOH / methanol / 0.08 h / 25 °C

6: 65 percent / DCC, H₃PO₄ / dimethylsulfoxide

7: 1.) acetone cyanohydrin, 2.) oxalyl chloride

8: 85 percent / NaBH₄

With potassium hydroxide; sodium tetrahydroborate; oxalyl dichloride; phosphoric acid; phosphorus tribromide; potassium carbonate; 2-hydroxy-2-methylpropanenitrile; dicyclohexyl-carbodiimide; In methanol; dimethyl sulfoxide;

DOI:10.1021/ja00539a038

Reference yield:

(4aR*,5S*,6S*,7R*)-2-benzyl-3,4,4a,5,6,7-hexahydro-5-((methoxymethoxy)methyl)-6,7-oxy-1(2H)-isoquinolone (96648-91-8) → (+/-)-3-isoreserpine (50-55-5,482-85-9,1263-58-7,6872-69-1,17138-19-1,17298-47-4,72151-85-0,72173-53-6,75331-15-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / lithium 2-ethylhexanoate / 1,2-dimethoxy-ethane / 16 h / Heating

2: 98 percent / Ag₂O, CaSO₄ / 96 h / Ambient temperature

3: acid / methanol

4: pyridinium dichromate / dimethylformamide

6: alane

7: methanol / acid

8: 40 percent / hydrogen

9: 91 percent / 4-(dimethylamino)pyridine / pyridine; CH₂Cl₂ / 24 h / Ambient temperature

10: 93 percent / hydrogen / 20 percent Pd(OH)2/C / acetic acid / 24 h / 760 Torr

11: 69 percent / N,N-diisopropylethylamine, NaI / dimethylsulfoxide / 72 h / Ambient temperature

12: 1.) Hg(OAc)2, 2.) H₂S, 3.) Zn / 1.) aq. acetic acid, 85-90 deg C, 1.25 h, 2.) aq. acetic acid, 85-90 deg C to rt, 1 h, 3.) aq. HClO₄, THF, acetone, reflux, 15 min

With methanol; dmap; calcium sulfate; dipyridinium dichromate; hydrogen sulfide; mercury(II) diacetate; hydrogen; aluminium hydride; lithium 2-ethylhexanoate; N-ethyl-N,N-diisopropylamine; sodium iodide; silver(l) oxide; zinc; palladium dihydroxide; In pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja00254a036

upstream raw materials:

reserpine

(1S,2R,3R,4aS,13bS,14aS)-8a-Hydroxy-2,11-dimethoxy-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

6-methoxy-tryptophyl bromide

2-(6-methoxy-1H-indol-3-yl)ethan-1-ol

Downstream raw materials:

reserpine

C₃₃H₄₂N₂O₉

2,3-secoreserpine

Refernces

• 1、 Stork, Gilbert,Tang, Peng Cho,Casey, Michael,Goodman, Burton,Toyota, Masahiro. "Regiospecific and stereoselective syntheses of (±)-reserpine and (-)-reserpine". . p. 16255 - 16262. Retrieved 2007/10/03.
• 2、 Zhang, Lin-Hua,Gupta, Ashok K.,Cook, James M.. "Reinvestigation of the Mechanism of the Acid-Catalyzed Epimerization of Reserpine to Isoreserpine". . p. 4708 - 4712. Retrieved 2007/10/02.