(1S,5R,6R)-8-Benzyl-6-hydroxymethyl-4-methylene-3,8-diaza-bicyclo[3.2.1]octan-2-one

Base Information

Chemical Name:(1S,5R,6R)-8-Benzyl-6-hydroxymethyl-4-methylene-3,8-diaza-bicyclo[3.2.1]octan-2-one
CAS No.:641627-87-4
Molecular Formula:C₁₅H₁₈N₂O₂
Molecular Weight:258.32
Hs Code.:

Synonyms:(1S,5R,6R)-8-Benzyl-6-hydroxymethyl-4-methylene-3,8-diaza-bicyclo[3.2.1]octan-2-one

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Chemical Property of (1S,5R,6R)-8-Benzyl-6-hydroxymethyl-4-methylene-3,8-diaza-bicyclo[3.2.1]octan-2-one

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Technology Process of (1S,5R,6R)-8-Benzyl-6-hydroxymethyl-4-methylene-3,8-diaza-bicyclo[3.2.1]octan-2-one

There total 1 articles about (1S,5R,6R)-8-Benzyl-6-hydroxymethyl-4-methylene-3,8-diaza-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:

: 8-Benzyl-6-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-4-methylene-3,8-diaza-bicyclo[3.2.1]octan-2-one

: (1R,5S,6S)-8-Benzyl-6-hydroxymethyl-4-methylene-3,8-diaza-bicyclo[3.2.1]octan-2-one

: 641627-87-4
(1S,5R,6R)-8-Benzyl-6-hydroxymethyl-4-methylene-3,8-diaza-bicyclo[3.2.1]octan-2-one

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 20 ℃; for 6h; Title compound not separated from byproducts;
DOI:10.1021/ja039223q

Reference yield:

: 641627-87-4
(1S,5R,6R)-8-Benzyl-6-hydroxymethyl-4-methylene-3,8-diaza-bicyclo[3.2.1]octan-2-one

: 641627-93-2
(1S,4S,5R,6R)-4-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-2-oxo-6-triisopropylsilanyloxymethyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-lutidine / CH₂Cl₂ / 1.25 h

2: ICl / CH₂Cl₂ / 0.75 h / 0 °C

3: MeOH; aq. K₂CO₃; Pd(PPh₃)4 / benzene / 3.5 h / 70 °C

4: CF₃CO₂H; H₂ / Pd/C / ethanol / 28 h / 51714.8 Torr

5: N,N-dimethylaminopyridine / acetonitrile / 0.67 h

6: potassium trimethylsilanoate / acetonitrile / 1.5 h / 20 °C

With 2,6-dimethylpyridine; methanol; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium trimethylsilonate; hydrogen; Iodine monochloride; potassium carbonate; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile; benzene; 3: Suzuki coupling;
DOI:10.1021/ja039223q

Reference yield:

: 641627-87-4
(1S,5R,6R)-8-Benzyl-6-hydroxymethyl-4-methylene-3,8-diaza-bicyclo[3.2.1]octan-2-one

: 641627-91-0
Toluene-4-sulfonic acid 2,4-dimethoxy-3-methyl-5-((1R,2S,5S,7R)-4-oxo-7-triisopropylsilanyloxymethyl-3,8-diaza-bicyclo[3.2.1]oct-2-ylmethyl)-phenyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / 1.25 h

2: ICl / CH₂Cl₂ / 0.75 h / 0 °C

3: MeOH; aq. K₂CO₃; Pd(PPh₃)4 / benzene / 3.5 h / 70 °C

4: CF₃CO₂H; H₂ / Pd/C / ethanol / 28 h / 51714.8 Torr

With 2,6-dimethylpyridine; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; Iodine monochloride; potassium carbonate; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; benzene; 3: Suzuki coupling;
DOI:10.1021/ja039223q