ipalbidine synthesis

3synthesis methods

Product Name:ipalbidine
CAS Number:26294-41-7
Molecular formula:C15H19NO
Molecular Weight:229.32

Benzeneacetic acid, α-methylene-4-(phenylmethoxy)-, methyl ester

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Yield:-

Steps:

Multi-step reaction with 9 steps
1: 1.) K(t-BuO) / 1.) 8percent aq. DMSO, 2.) aq. DMSO, 3h, 20 deg C
2: 74 percent / H₂ / 5percent Pd/c / ethanol / 21 h / Ambient temperature
3: 86 percent / N-methylmorpholine / CH₂Cl₂ / 1 h, 0 deg C, then 30 min, room t.
4: N-methylmorpholine / diethyl ether / 40 min, 0 deg C, then 50 min, room t.
5: diethyl ether / 0 deg C, then 16 h, room t.
6: 82 percent / Rh(OAc)2 / CH₂Cl₂ / 1.5 h / Ambient temperature
7: 7 percent / H₂ / Rh/act. Al₂O₃ / ethanol / 5 h / 50 °C / 3102.9 Torr
8: 1.) THF, 24 h, room t., 2.) THF
9: 48percent aq. HBr / 1 h / 80 °C

References:

Jefford, Charles W.;Kubota, Tadatoshi;Zaslona, Alexander [Helvetica Chimica Acta,1986,vol. 69,p. 2048 - 2061]

Indolizine, 1,2,3,5,8,8a-hexahydro-6-(4-methoxyphenyl)-7-methyl-

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References

7-Indolizinol, 6-[4-(acetyloxy)phenyl]octahydro-7-methyl-, 7-acetate

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References