(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

Base Information

Chemical Name:(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone
CAS No.:168773-46-4
Molecular Formula:C₂₀H₃₂BrNO₃Si
Molecular Weight:442.468
Hs Code.:

Synonyms:(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

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Chemical Property of (5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

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Technology Process of (5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

There total 9 articles about (5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone 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: 89.0%

: 168773-44-2
(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(hydroxymethyl)-2-piperidinone

: 168773-46-4
(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane; 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h;
DOI:10.1021/jo00119a044

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 168773-46-4
(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 15 h

2: 97 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h

3: 100 percent / H₂ / 10percent Pd/C / ethanol / 23 h

4: 89 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h

With 1H-imidazole; carbon tetrabromide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00119a044

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 168773-46-4
(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h

2: 100 percent / H₂ / 10percent Pd/C / ethanol / 23 h

3: 89 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h

With carbon tetrabromide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jo00119a044