[(1S,5R,7R)-7-Allyl-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-phenyl-methanone

Base Information

Chemical Name:[(1S,5R,7R)-7-Allyl-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-phenyl-methanone
CAS No.:289710-30-1
Molecular Formula:C₂₃H₃₃NO₂Si
Molecular Weight:383.606
Hs Code.:

Synonyms:[(1S,5R,7R)-7-Allyl-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-phenyl-methanone

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Chemical Property of [(1S,5R,7R)-7-Allyl-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-phenyl-methanone

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Technology Process of [(1S,5R,7R)-7-Allyl-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-phenyl-methanone

There total 12 articles about [(1S,5R,7R)-7-Allyl-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-phenyl-methanone 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: 91.0%

: 289710-29-8
[(1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-phenyl-methanone

: 762-72-1
allyl-trimethyl-silane

: 289710-30-1
[(1S,5R,7R)-7-Allyl-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-phenyl-methanone

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/jo000260z

Reference yield:

: 261156-79-0
(E)-3-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-acrylonitrile

: 289710-30-1
[(1S,5R,7R)-7-Allyl-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-phenyl-methanone

Guidance literature:: Multi-step reaction with 11 steps

1: 98 percent / H₂ / Pd/C / ethyl acetate / 12 h / 760.05 Torr

2: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

3: 84 percent / Jones reagent / acetone / 0.5 h / 20 °C

4: 78 percent / SmI₂; MeOH / tetrahydrofuran / -78 - 20 °C

5: 91 percent / DIPEA / CH₂Cl₂ / 17 h / 0 - 20 °C

6: methanol / 20 h / 0 - 20 °C

7: 1.3 g / NaH / toluene / 3 h / Heating

8: Na; naphthalene / 1,2-dimethoxy-ethane / 0.25 h / -78 °C

9: 0.59 g / DMAP / acetonitrile / 0 - 20 °C

10: 59 percent / NaNO₂; CuCl; HCl / 1 h / 20 °C

11: 91 percent / TiCl₄ / CH₂Cl₂ / -78 - 20 °C

With hydrogenchloride; methanol; dmap; jones reagent; samarium diiodide; naphthalene; tetrabutyl ammonium fluoride; hydrogen; sodium; titanium tetrachloride; sodium hydride; N-ethyl-N,N-diisopropylamine; copper(l) chloride; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; 1: Catalytic hydrogenation / 2: desilylation / 3: Oxidation / 4: Cyclization / 5: Condensation / 6: Condensation / 7: Reduction / 8: Reduction / 9: Acylation / 10: Oxidation / 11: Substitution;
DOI:10.1021/jo000260z

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 289710-30-1
[(1S,5R,7R)-7-Allyl-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-phenyl-methanone

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / DIPEA / CH₂Cl₂ / 17 h / 0 - 20 °C

2: methanol / 20 h / 0 - 20 °C

3: 1.3 g / NaH / toluene / 3 h / Heating

4: Na; naphthalene / 1,2-dimethoxy-ethane / 0.25 h / -78 °C

5: 0.59 g / DMAP / acetonitrile / 0 - 20 °C

6: 59 percent / NaNO₂; CuCl; HCl / 1 h / 20 °C

7: 91 percent / TiCl₄ / CH₂Cl₂ / -78 - 20 °C

With hydrogenchloride; dmap; naphthalene; sodium; titanium tetrachloride; sodium hydride; N-ethyl-N,N-diisopropylamine; copper(l) chloride; sodium nitrite; In methanol; 1,2-dimethoxyethane; dichloromethane; toluene; acetonitrile; 1: Condensation / 2: Condensation / 3: Reduction / 4: Reduction / 5: Acylation / 6: Oxidation / 7: Substitution;
DOI:10.1021/jo000260z