Ephedradine A

Base Information

• Chemical Name: Ephedradine A
• CAS No.: 71461-13-7
• Molecular Formula: C28H36 N4 O4
• Molecular Weight: 492.618
• UNII: J1E0LYG58A
• DSSTox Substance ID: DTXSID501031984
• Nikkaji Number: J1.221.886I
• Wikidata: Q27281023
• Mol file: 71461-13-7.mol

Synonyms:11-epi-orantine;ephedradine A;orantine

Chemical Property of Ephedradine A

Chemical Property:

• Vapor Pressure: 5.06E-23mmHg at 25°C
• Boiling Point: 746.1°C at 760 mmHg
• Flash Point: 405°C
• PSA: 102.93000
• Density: 1.29g/cm³
• LogP: 3.67660
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 492.27365564
• Heavy Atom Count: 36
• Complexity: 743

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CCCNC(=O)CC(C3=CC4=C(C=C3)OC(C4C2=O)C5=CC=C(C=C5)O)NCCCNC1
• Isomeric SMILES: C1CCN2CCCNC(=O)C[C@@H](C3=CC4=C(C=C3)O[C@H]([C@@H]4C2=O)C5=CC=C(C=C5)O)NCCCNC1

Technology Process of Ephedradine A

There total 52 articles about Ephedradine A 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: 73.0%

O-benzyloxy-N1-benzyloxycarbonyl-ephedradine A (566203-08-5) → (-)-ephedradine A (71461-13-7)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/ja036011k

Reference yield:

N-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-N-(3-hydroxy-propyl)-2-nitro-benzenesulfonamide (566202-76-4) → (-)-ephedradine A (71461-13-7)

Guidance literature:

Multi-step reaction with 26 steps

1: 96 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran; toluene / 0 - 20 °C

2: 88 percent / PhSH; K₂CO₃ / dimethylformamide; acetonitrile / 0.67 h / 50 °C

3: 67 percent / Me₂AlCl / CH₂Cl₂ / 3 h / Heating

4: 88 percent / pyridine / 0 - 20 °C

5: 84 percent / Pd(OAc)2; tris(o-tolyl)phosphine / dimethylformamide / 24 h / 100 °C

6: 66 percent / (DHQD)2PHAL; K₂OsO₂(OH)4 / propan-1-ol; H₂O / 4 h / 20 °C

7: 87 percent / CCl₄; PPh₃ / toluene / 2 h / 100 °C

8: ammonium formate / Pd/C / methanol / 1.25 h / 60 °C

9: 118 mg / diethyl azodicarboxylate; PPh₃ / toluene / 2 h / 60 °C

10: 72 percent / aq. Na₂CO₃ / CH₂Cl₂ / 4 h

11: 95 percent / diethyl azodicarboxylate; PPh₃ / toluene / 1 h / 60 °C

12: 93 percent / PhSH; aq. KOH / acetonitrile / 2 h / 60 °C

13: 91 percent / aq. NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

14: 94 percent / CSA / methanol / 0.33 h / 20 °C

15: 100 percent / diethyl azodicarboxylate; PPh₃ / toluene; tetrahydrofuran / 0 - 20 °C

16: 84 percent / aq. HF / acetonitrile / 1.5 h

17: 77 percent / diethyl azodicarboxylate; PPh₃ / toluene / 0 - 20 °C

18: 96 percent / K₂CO₃ / methanol; tetrahydrofuran / 1 h / 20 °C

19: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

20: 77.9 mg / NaN₃ / dimethylformamide / 0.5 h / 60 °C

21: 97 percent / aq. LiOH / methanol; tetrahydrofuran / 5 h

22: 93 percent / WSCD*HCl / CH₂Cl₂ / 0 - 20 °C

23: PPh₃ / toluene / 4 h / Heating

24: 69.3 mg / H₂O / acetonitrile / 60 h / Heating

25: 75 percent / PhSH; aq. KOH / acetonitrile / 1.17 h / 50 °C

26: 73 percent / BCl₃ / CH₂Cl₂ / -78 - 0 °C

With pyridine; tetrachloromethane; palladium diacetate; potassium hydroxide; lithium hydroxide; sodium azide; potassium dioxotetrahydroxoosmate(VI); WSCD*HCl; camphor-10-sulfonic acid; hydrogen fluoride; water; ammonium formate; dimethylaluminum chloride; boron trichloride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; thiophenol; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Mitsunobu reaction / 5: Heck reaction / 6: Sharpless aminohydroxylation / 9: Mitsunobu reaction / 11: Mitsunobu reaction / 15: Mitsunobu reaction / 17: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.06.144

Reference yield:

(2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid (566202-75-3) → (-)-ephedradine A (71461-13-7)

Guidance literature:

Multi-step reaction with 26 steps

1: 96 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran; toluene / 0 - 20 °C

2: 88 percent / PhSH; K₂CO₃ / dimethylformamide; acetonitrile / 0.67 h / 50 °C

3: 67 percent / Me₂AlCl / CH₂Cl₂ / 3 h / Heating

4: 88 percent / pyridine / 0 - 20 °C

5: 84 percent / Pd(OAc)2; tris(o-tolyl)phosphine / dimethylformamide / 24 h / 100 °C

6: 66 percent / (DHQD)2PHAL; K₂OsO₂(OH)4 / propan-1-ol; H₂O / 4 h / 20 °C

7: 87 percent / CCl₄; PPh₃ / toluene / 2 h / 100 °C

8: ammonium formate / Pd/C / methanol / 1.25 h / 60 °C

9: 118 mg / diethyl azodicarboxylate; PPh₃ / toluene / 2 h / 60 °C

10: 72 percent / aq. Na₂CO₃ / CH₂Cl₂ / 4 h

11: 95 percent / diethyl azodicarboxylate; PPh₃ / toluene / 1 h / 60 °C

12: 93 percent / PhSH; aq. KOH / acetonitrile / 2 h / 60 °C

13: 91 percent / aq. NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

14: 94 percent / CSA / methanol / 0.33 h / 20 °C

15: 100 percent / diethyl azodicarboxylate; PPh₃ / toluene; tetrahydrofuran / 0 - 20 °C

16: 84 percent / aq. HF / acetonitrile / 1.5 h

17: 77 percent / diethyl azodicarboxylate; PPh₃ / toluene / 0 - 20 °C

18: 96 percent / K₂CO₃ / methanol; tetrahydrofuran / 1 h / 20 °C

19: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

20: 77.9 mg / NaN₃ / dimethylformamide / 0.5 h / 60 °C

21: 97 percent / aq. LiOH / methanol; tetrahydrofuran / 5 h

22: 93 percent / WSCD*HCl / CH₂Cl₂ / 0 - 20 °C

23: PPh₃ / toluene / 4 h / Heating

24: 69.3 mg / H₂O / acetonitrile / 60 h / Heating

25: 75 percent / PhSH; aq. KOH / acetonitrile / 1.17 h / 50 °C

26: 73 percent / BCl₃ / CH₂Cl₂ / -78 - 0 °C

With pyridine; tetrachloromethane; palladium diacetate; potassium hydroxide; lithium hydroxide; sodium azide; potassium dioxotetrahydroxoosmate(VI); WSCD*HCl; camphor-10-sulfonic acid; hydrogen fluoride; water; ammonium formate; dimethylaluminum chloride; boron trichloride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; thiophenol; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Mitsunobu reaction / 5: Heck reaction / 6: Sharpless aminohydroxylation / 9: Mitsunobu reaction / 11: Mitsunobu reaction / 15: Mitsunobu reaction / 17: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.06.144

upstream raw materials:

(11S,17S,18S)-aphelandrine

(-)-(8S)-1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-8-(4-hydroxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one

O-benzyloxy-N₁-benzyloxycarbonyl-ephedradine A

p-benzyloxybenzaldehyde

Downstream raw materials:

(1S,18²R,18³R)-18²-(3,5-dibromo-4-hydroxy-phenyl)-18^2,3-dihydro-2,6,11,15-tetraaza-18(5,3)-benzofurana-bicyclo[9.6.2]nonadecaphane-16,19-dione