(1S,3aS,5aS,6R,11bS,11cS)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indol-2-one

Base Information

Chemical Name:(1S,3aS,5aS,6R,11bS,11cS)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indol-2-one
CAS No.:1331828-08-0
Molecular Formula:C₃₁H₃₆N₂O₄
Molecular Weight:500.638
Hs Code.:

(1S,3aS,5aS,6R,11bS,11cS)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indol-2-one

Synonyms:(1S,3aS,5aS,6R,11bS,11cS)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indol-2-one

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Chemical Property of (1S,3aS,5aS,6R,11bS,11cS)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indol-2-one

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Technology Process of (1S,3aS,5aS,6R,11bS,11cS)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indol-2-one

There total 3 articles about (1S,3aS,5aS,6R,11bS,11cS)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indol-2-one 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: 77.0%

: 1331828-07-9
(5R,6R,7S,9R,13S,14R)-N-benzyl-17-(cyclopropylmethyl)-4,5-epoxy-6-hydroxy-3-methoxy-6,14-ethanomorphinan-7-carboxamide

: 1331828-08-0
(1S,3aS,5aS,6R,11bS,11cS)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indol-2-one

Guidance literature:: (5R,6R,7S,9R,13S,14R)-N-benzyl-17-(cyclopropylmethyl)-4,5-epoxy-6-hydroxy-3-methoxy-6,14-ethanomorphinan-7-carboxamide; With sodium hydride; In cyclopentyl methyl ether; for 3h; Inert atmosphere; Reflux;

With water; sodium hydrogencarbonate; In cyclopentyl methyl ether;
DOI:10.1016/j.tet.2011.04.097

Reference yield: 77.0%

: 1331828-08-0
(1S,3aS,5aS,6R,11bS,11cS)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indol-2-one

Guidance literature:: With potassium tert-butylate; In tert-butyl alcohol; for 1h; Inert atmosphere; Reflux;

Reference yield:

: 17-(cyclopropylmethyl)-4,5α-epoxy-3,6β-dihydroxy-6,14-endoethenomorphinan-7α-(N-benzyl)carboxamide

: 1331828-08-0
(1S,3aS,5aS,6R,11bS,11cS)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-methanonaphtho[1,2-e]indol-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: potassium carbonate / N,N-dimethyl-formamide / 30 h / 20 °C / Inert atmosphere; Darkness

2: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 50 °C / 3750.38 Torr

3: sodium hydride / cyclopentyl methyl ether / 3 h / Inert atmosphere; Reflux

With palladium 10% on activated carbon; hydrogen; sodium hydride; potassium carbonate; In methanol; cyclopentyl methyl ether; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2011.04.097