(+/-)-paliclavine

Base Information

Chemical Name:(+/-)-paliclavine
CAS No.:79732-85-7
Molecular Formula:C₁₆H₂₀N₂O
Molecular Weight:256.348
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+/-)-paliclavine

Chemical Property:

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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%

: 79681-14-4,79732-84-6
(9R,9aR)-9-Isopropenyl-7-methyl-4,6,6a,7,9,9a-hexahydro-8-oxa-4,7-diaza-cyclopenta[e]acenaphthylene

: 52052-66-1
(+)-paliclavine

: 79732-85-7
5-epi-paliclavine

Guidance literature:: With aluminum amalgam; In tetrahydrofuran; water;
DOI:10.1016/0040-4020(84)80018-6

Reference yield: 17.0%

: 89368-45-6,89396-48-5
t-butyl(4R^*,5S^*,1'R^*)-N-<5-(2'-methyl-2'-propen-1'-ol)-1,3,4,5-tetrahydrobenzindolyl>N-methylcarbamate

: 52052-66-1,79732-85-7,89396-47-4
(+/-)-paliclavine

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1016/S0040-4020(01)88608-7

Reference yield:

: 16136-52-0
4-cyanoindole

: 52052-66-1,79732-85-7,89396-47-4
(+/-)-paliclavine

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