N-benzyl-N,8β-ethano-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine quaternary chloride salt

Base Information

Chemical Name:N-benzyl-N,8β-ethano-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine quaternary chloride salt
CAS No.:110143-36-7
Molecular Formula:C₃₆H₄₈NO₄Si*Cl
Molecular Weight:622.32
Hs Code.:

Synonyms:N-benzyl-N,8β-ethano-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine quaternary chloride salt

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Chemical Property of N-benzyl-N,8β-ethano-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine quaternary chloride salt

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Technology Process of N-benzyl-N,8β-ethano-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine quaternary chloride salt

There total 10 articles about N-benzyl-N,8β-ethano-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine quaternary chloride salt 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: 100.0%

: 110173-26-7
N-benzyl-8β-(2-hydroxyethyl)-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine

: 110143-36-7
N-benzyl-N,8β-ethano-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine quaternary chloride salt

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h;
DOI:10.1021/jm00394a016

Reference yield:

: 93-97-0
benzoic acid anhydride

: 110143-36-7
N-benzyl-N,8β-ethano-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine quaternary chloride salt

Guidance literature:: Multi-step reaction with 10 steps

1: 84 percent / Et₃N / CH₂Cl₂ / Ambient temperature

2: 99 percent / benzene / 7 h / Heating

3: 64 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating

4: 1.) KH, 2.) n-BuLi

5: 97 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 - -40 °C

6: 52 percent / silica gel / CHCl₃ / 48 h

7: 84 percent / tetrahydrofuran / 25 h / Ambient temperature

8: 89 percent / KH / tetrahydrofuran / 24 h / Ambient temperature

9: 1.) BH₃*THF, 2.) aq. NaOH, H₂O₂ / 1.) RT, 1 h, 2.) THF, RT, 3.5 h

10: 100 percent / Et₃N, methanesulfonyl chloride / CH₂Cl₂ / 0.08 h / 0 °C

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; borane-THF; oxalyl dichloride; dihydrogen peroxide; silica gel; potassium hydride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; benzene;
DOI:10.1021/jm00394a016

Reference yield:

: 110173-63-2
N-benzoylnorthebaine

: 110143-36-7
N-benzyl-N,8β-ethano-7α-<<(tert-butyldimethylsilyl)oxy>-methyl>-endo-ethylenetetrahydronorthebaine quaternary chloride salt

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / benzene / 7 h / Heating

2: 64 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating

3: 1.) KH, 2.) n-BuLi

4: 97 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 - -40 °C

5: 52 percent / silica gel / CHCl₃ / 48 h

6: 84 percent / tetrahydrofuran / 25 h / Ambient temperature

7: 89 percent / KH / tetrahydrofuran / 24 h / Ambient temperature

8: 1.) BH₃*THF, 2.) aq. NaOH, H₂O₂ / 1.) RT, 1 h, 2.) THF, RT, 3.5 h

9: 100 percent / Et₃N, methanesulfonyl chloride / CH₂Cl₂ / 0.08 h / 0 °C

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; borane-THF; oxalyl dichloride; dihydrogen peroxide; silica gel; potassium hydride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; benzene;
DOI:10.1021/jm00394a016