3-(benzyloxy)-4,5α-epoxy-14-hydroxy-6β-(2-aminoethoxy)-17-(cyclopropylmethyl)morphinan

Base Information

Chemical Name:3-(benzyloxy)-4,5α-epoxy-14-hydroxy-6β-(2-aminoethoxy)-17-(cyclopropylmethyl)morphinan
CAS No.:141555-50-2
Molecular Formula:C₂₉H₃₆N₂O₄
Molecular Weight:476.616
Hs Code.:

Synonyms:3-(benzyloxy)-4,5α-epoxy-14-hydroxy-6β-(2-aminoethoxy)-17-(cyclopropylmethyl)morphinan

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Chemical Property of 3-(benzyloxy)-4,5α-epoxy-14-hydroxy-6β-(2-aminoethoxy)-17-(cyclopropylmethyl)morphinan

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Technology Process of 3-(benzyloxy)-4,5α-epoxy-14-hydroxy-6β-(2-aminoethoxy)-17-(cyclopropylmethyl)morphinan

There total 6 articles about 3-(benzyloxy)-4,5α-epoxy-14-hydroxy-6β-(2-aminoethoxy)-17-(cyclopropylmethyl)morphinan 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: 79.0%

: 141555-49-9
3-(benzyloxy)-4,5α-epoxy-14-hydroxy-6β-(2-oximidoethoxy)-17-(cyclopropylmethyl)morphinan

: 141555-50-2
3-(benzyloxy)-4,5α-epoxy-14-hydroxy-6β-(2-aminoethoxy)-17-(cyclopropylmethyl)morphinan

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 80 ℃; for 2h;
DOI:10.1021/jm00091a005

Reference yield:

: 49625-89-0
β-naltrexol

: 141555-50-2
3-(benzyloxy)-4,5α-epoxy-14-hydroxy-6β-(2-aminoethoxy)-17-(cyclopropylmethyl)morphinan

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / tetra-n-butylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂ / 5 h

2: 1.) KH / 1.) THF, 4 h, 2.)a) THF, 15 h, b) 50 deg C, 2 h

3: 99 percent / 10percent aq. oxalic acid / 0.5 h / 50 °C

4: 97 percent / hydroxylamine hydrochloride, NaHCO₃ / methanol; H₂O / 2 h

5: 79 percent / LiAlH₄ / tetrahydrofuran / 2 h / 80 °C

With sodium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; tetra(n-butyl)ammonium hydrogensulfate; oxalic acid; potassium hydride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jm00091a005

Reference yield:

: 100-39-0
benzyl bromide

: 141555-50-2
3-(benzyloxy)-4,5α-epoxy-14-hydroxy-6β-(2-aminoethoxy)-17-(cyclopropylmethyl)morphinan

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / tetra-n-butylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂ / 5 h

2: 1.) KH / 1.) THF, 4 h, 2.)a) THF, 15 h, b) 50 deg C, 2 h

3: 99 percent / 10percent aq. oxalic acid / 0.5 h / 50 °C

4: 97 percent / hydroxylamine hydrochloride, NaHCO₃ / methanol; H₂O / 2 h

5: 79 percent / LiAlH₄ / tetrahydrofuran / 2 h / 80 °C

With sodium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; tetra(n-butyl)ammonium hydrogensulfate; oxalic acid; potassium hydride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jm00091a005