(+/-)-paliclavine

Base Information

• Chemical Name: (+/-)-paliclavine
• CAS No.: 79732-85-7
• Molecular Formula: C₁₆H₂₀N₂O
• Molecular Weight: 256.348
• Mol file: 79732-85-7.mol

Synonyms:

Chemical Property of (+/-)-paliclavine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-paliclavine

There total 15 articles about (+/-)-paliclavine 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: 21.3%

(9R,9aR)-9-Isopropenyl-7-methyl-4,6,6a,7,9,9a-hexahydro-8-oxa-4,7-diaza-cyclopenta[e]acenaphthylene (79681-14-4,79732-84-6) → (+)-paliclavine (52052-66-1) + 5-epi-paliclavine (79732-85-7)

Guidance literature:

With aluminum amalgam; In tetrahydrofuran; water;

DOI:10.1016/0040-4020(84)80018-6

Reference yield: 17.0%

t-butyl(4R*,5S*,1'R*)-N-<5-(2'-methyl-2'-propen-1'-ol)-1,3,4,5-tetrahydrobenzindolyl>N-methylcarbamate (89368-45-6,89396-48-5) → (+/-)-paliclavine (52052-66-1,79732-85-7,89396-47-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4020(01)88608-7

Reference yield:

4-cyanoindole (16136-52-0) → (+/-)-paliclavine (52052-66-1,79732-85-7,89396-47-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 91 percent / sodium hypophosphite / Raney Ni / pyridine; acetic acid; H₂O / 2 h / 45 - 50 °C

2: 1.) NaH / 1.) THF, 0 deg C, then RT, 30 min; 2.) THF, RT, 1.5 h

3: 1.) Me₂NH; 2.) MeI / 1.) AcOH, 0 deg C, then RT, 18 h; 2.) i-PrOH, water, 0 deg C, then RT, 72 h

4: sodium hypophosphite, Raney Ni / pyridine; acetic acid; H₂O / 5.5 h / 60 °C

5: methanol / 1.) 70 deg C, 2 h; 2.) RT, 16 h

6: various solvent(s) / 1 h / Heating; 1,2-dichlorobenzene, equilibrium

7: 96 percent / LiAlH₄ / tetrahydrofuran / 0.23 h / Ambient temperature

8: Raney Ni, NEt₃ / tetrahydrofuran; methanol / 16 h / Ambient temperature

9: 100 percent / NaIO₄ / H₂O; methanol / 0.25 h / 0 °C

10: 99 percent / i-Pr₂NEt / CHCl₃ / 3 h / Ambient temperature

11: tetrahydrofuran / 0.25 h / Ambient temperature

12: 17 percent / CF₃COOH / CH₂Cl₂ / 0.25 h / 0 °C

With sodium periodate; lithium aluminium tetrahydride; sodium hypophosphite; nickel; sodium hydride; dimethyl amine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; methyl iodide; nickel; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetic acid;

DOI:10.1016/S0040-4020(01)88608-7

upstream raw materials:

(9R,9aR)-9-Isopropenyl-7-methyl-4,6,6a,7,9,9a-hexahydro-8-oxa-4,7-diaza-cyclopenta[e]acenaphthylene

t-butyl(4R^*,5S^*,1'R^*)-N-<5-(2'-methyl-2'-propen-1'-ol)-1,3,4,5-tetrahydrobenzindolyl>N-methylcarbamate

4-formyl indole

4-cyanoindole