N-phenylmethyl-7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-amine

Base Information

Chemical Name:N-phenylmethyl-7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-amine
CAS No.:303175-87-3
Molecular Formula:C₄₀H₄₄N₂O₂Si
Molecular Weight:612.887
Hs Code.:

Synonyms:N-phenylmethyl-7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-amine

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Chemical Property of N-phenylmethyl-7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-amine

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Technology Process of N-phenylmethyl-7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-amine

There total 4 articles about N-phenylmethyl-7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-amine 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: 83.6%

: 100-46-9
benzylamine

: 303175-81-7
7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-ol, 3-(trifluoromethanesulfonate)

: 303175-87-3
N-phenylmethyl-7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-amine

Guidance literature:: With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 80 ℃; for 8h;
DOI:10.1021/jm000119i

Reference yield:

: 303175-80-6
7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-ol

: 303175-87-3
N-phenylmethyl-7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-amine

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 83.6 percent / BINAP; Pd(OAc)2; NaOt-Bu / toluene / 8 h / 80 °C

With pyridine; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In dichloromethane; toluene; 1: Condensation / 2: Substitution;
DOI:10.1021/jm000119i

Reference yield:

: 303175-79-3
7,8-didehydro-3,6-bis[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan

: 303175-87-3
N-phenylmethyl-7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-amine

Guidance literature:: Multi-step reaction with 3 steps

1: 84.1 percent / TBAF; H₂O / tetrahydrofuran / 1 h / 25 °C

2: 100 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

3: 83.6 percent / BINAP; Pd(OAc)2; NaOt-Bu / toluene / 8 h / 80 °C

With pyridine; palladium diacetate; tetrabutyl ammonium fluoride; water; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In tetrahydrofuran; dichloromethane; toluene; 1: Desilylation / 2: Condensation / 3: Substitution;
DOI:10.1021/jm000119i