(1R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octan-2-one

Base Information

Chemical Name:(1R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octan-2-one
CAS No.:261157-05-5
Molecular Formula:C₂₀H₃₁NO₄SSi
Molecular Weight:409.622
Hs Code.:

Synonyms:(1R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octan-2-one

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Chemical Property of (1R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octan-2-one

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Technology Process of (1R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octan-2-one

There total 9 articles about (1R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octan-2-one 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%

: 69739-34-0
t-butyldimethylsiyl triflate

: 261156-81-4
(1R,5R)-1-Hydroxy-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octan-2-one

: 261157-05-5
(1R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octan-2-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1002/(SICI)1521-3773(20000103)39

Reference yield:

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

: 261157-05-5
(1R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octan-2-one

Guidance literature:: Multi-step reaction with 5 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

With methanol; jones reagent; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone; 1: Catalytic hydrogenation / 2: desilylation / 3: Oxidation / 4: Cyclization / 5: Condensation;
DOI:10.1021/jo000260z

Reference yield:

: 261156-80-3
3-[(R)-4-Oxo-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionitrile

: 261157-05-5
(1R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / SmI₂; MeOH / tetrahydrofuran / -78 - 20 °C

2: 91 percent / DIPEA / CH₂Cl₂ / 17 h / 0 - 20 °C

With methanol; samarium diiodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Cyclization / 2: Condensation;
DOI:10.1021/jo000260z