Methyl lysergate

Base Information

• Chemical Name: Methyl lysergate
• CAS No.: 4579-64-0
• Molecular Formula: C17H18N2O2
• Molecular Weight: 282.342
• NSC Number: 157966
• Wikipedia: Lysergic_acid_methyl_ester
• ChEMBL ID: CHEMBL1334149
• Mol file: 4579-64-0.mol

Synonyms:Methyl lysergate;MLS000756286;SMR000528662;Methyl D-lysergate;methyl 7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate;Lysergic acid methyl ester;NSC-157966;cid_98965;CHEMBL1334149;BDBM51255;RNHDWLRHUJZABX-UHFFFAOYSA-N;NSC157966;NCGC00246956-01;Ergoline-8.beta.-carboxylic acid,10-didehydro-6-methyl-, methyl ester;7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxylic acid methyl ester;Ergoline-8-carboxylic acid,10-didehydro-6-methyl-, methyl ester, (8.beta.)-

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Chemical Property of Methyl lysergate

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 282.136827821
• Heavy Atom Count: 21
• Complexity: 475

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)C(=O)OC

Technology Process of Methyl lysergate

There total 46 articles about Methyl lysergate 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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + C16H16N2O2 (87332-72-7) → iso-lysergic acid methyl ester (67215-36-5) + lysergic acid methyl ester (4579-64-0)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 1h; Overall yield = 168.3 mg; Inert atmosphere;

DOI:10.1021/ol4019562

Reference yield:

(S)-4-benzyl-3-((S)-2-((S)-hydroxy(1-tosyl-1H-indol-3-yl)methyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one (1449117-92-3) → iso-lysergic acid methyl ester (67215-36-5) + lysergic acid methyl ester (4579-64-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: hydrazine hydrate / tetrahydrofuran / 1 h / 0 °C

2.1: hydrogenchloride; tert.-butylnitrite / ethyl acetate; isopropyl alcohol / 1 h / 60 °C / Inert atmosphere

3.1: titanium tetrachloride; triethylsilane / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / Inert atmosphere

5.1: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 80 °C / Inert atmosphere

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; silver carbonate / toluene / 4 h / 100 °C / Inert atmosphere

8.1: methanol; magnesium / benzene / 1 h / 20 °C / Inert atmosphere

9.1: dmap / acetonitrile / 1 h / 20 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

11.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / Inert atmosphere

12.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C

13.1: diethyl ether; methanol / 0.25 h / 20 °C / Inert atmosphere

14.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / Inert atmosphere

15.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / Inert atmosphere

15.2: 0.5 h / 50 °C / Inert atmosphere

16.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; methanol; triethylsilane; dmap; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; dimethylsulfide; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; titanium tetrachloride; sodium cyanoborohydride; sodium hydrogencarbonate; hydrazine hydrate; magnesium; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; ethyl acetate; isopropyl alcohol; toluene; acetonitrile; tert-butyl alcohol; benzene; 7.1: |Heck Reaction;

DOI:10.1021/ol4019562

Reference yield:

(S)-2-((S)-(4-bromo-1-tosyl-1H-indol-3-yl)(hydroxy)methyl)but-3-enehydrazide (1449117-93-4) → iso-lysergic acid methyl ester (67215-36-5) + lysergic acid methyl ester (4579-64-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: hydrogenchloride; tert.-butylnitrite / ethyl acetate; isopropyl alcohol / 1 h / 60 °C / Inert atmosphere

2.1: titanium tetrachloride; triethylsilane / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / Inert atmosphere

4.1: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 80 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; silver carbonate / toluene / 4 h / 100 °C / Inert atmosphere

7.1: methanol; magnesium / benzene / 1 h / 20 °C / Inert atmosphere

8.1: dmap / acetonitrile / 1 h / 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

10.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / Inert atmosphere

11.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C

12.1: diethyl ether; methanol / 0.25 h / 20 °C / Inert atmosphere

13.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / Inert atmosphere

14.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / Inert atmosphere

14.2: 0.5 h / 50 °C / Inert atmosphere

15.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; methanol; triethylsilane; dmap; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; dimethylsulfide; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; titanium tetrachloride; sodium cyanoborohydride; sodium hydrogencarbonate; magnesium; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; ethyl acetate; isopropyl alcohol; toluene; acetonitrile; tert-butyl alcohol; benzene; 6.1: |Heck Reaction;

DOI:10.1021/ol4019562

upstream raw materials:

diazomethane

D-lysergic acid

N-[(7-methyl-6,6a,7,8-tetrahydro-4H-indolo[4,3-fg]quinolin-9-ylidene)-(toluene-4-sulfonyl)-methyl]-formamide

methanol

Downstream raw materials:

(5R,8R)-6-methyl-8β-hydroxymethyl-9α-hydroxyergoline

6-cyano-9,10-didehydro-ergoline-8-carboxylic acid methyl ester

(+/-)-lysergic acid hydrazide

toluene-4-sulfonic acid 2-[(6aR,9R)-7-phenylcarbamoyl-9-(pyrrolidine-1-carbonyl)-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl]-ethyl ester

Refernces

• 1、 Smith,Timmis. "-". . p. 1440. Retrieved 1936.
• 2、 Umezaki, Satoshi,Yokoshima, Satoshi,Fukuyama, Tohru. "Erratum :Total synthesis of lysergic acid (Organic Letters (2014 ) 16:4 (1269-1269))". . p. 4692 - 4692. Retrieved 2015/03/18.
• 3、 Inuki, Shinsuke,Iwata, Akira,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki. "Enantioselective total synthesis of (+)-lysergic acid, (+)-lysergol, and (+)-isolysergol by palladium-catalyzed domino cyclization of allenes bearing amino and bromoindolyl groups". experimental part. p. 2072 - 2083. Retrieved 2011/05/12.