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

Base Information

Chemical Name:(2-Amino-phenyl)-[(1S,5R)-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-methanone
CAS No.:289710-28-7
Molecular Formula:C₂₀H₃₀N₂O₂Si
Molecular Weight:358.556
Hs Code.:

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

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

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

There total 10 articles about (2-Amino-phenyl)-[(1S,5R)-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-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:

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

: 289710-28-7
(2-Amino-phenyl)-[(1S,5R)-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-methanone

Guidance literature:: Multi-step reaction with 9 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

With methanol; dmap; jones reagent; samarium diiodide; naphthalene; tetrabutyl ammonium fluoride; hydrogen; sodium; sodium hydride; N-ethyl-N,N-diisopropylamine; 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;
DOI:10.1021/jo000260z

Reference yield:

: 118-48-9
isatoic anhydride

: (1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-ene

: 289710-28-7
(2-Amino-phenyl)-[(1S,5R)-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-methanone

Guidance literature:: With dmap; In acetonitrile; at 0 - 20 ℃;
DOI:10.1021/jo000260z

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 289710-28-7
(2-Amino-phenyl)-[(1S,5R)-1-(tert-butyl-dimethyl-silanyloxy)-6-aza-bicyclo[3.2.1]oct-2-en-6-yl]-methanone

Guidance literature:: Multi-step reaction with 5 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

With dmap; naphthalene; sodium; sodium hydride; N-ethyl-N,N-diisopropylamine; In methanol; 1,2-dimethoxyethane; dichloromethane; toluene; acetonitrile; 1: Condensation / 2: Condensation / 3: Reduction / 4: Reduction / 5: Acylation;
DOI:10.1021/jo000260z