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

Base Information

• Chemical Name: (5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone
• CAS No.: 168773-45-3
• Molecular Formula: C₁₉H₃₀BrNO₂Si
• Molecular Weight: 412.442
• Mol file: 168773-45-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 9 articles about (5S,6R)-1-Benzyl-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: 93.0%

(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(hydroxymethyl)-2-piperidinone (168773-41-9) → (5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone (168773-45-3)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h;

DOI:10.1021/jo00119a044

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone (168773-45-3)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 15 h

2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h

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

4: 93 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 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:

benzyl bromide (100-39-0) → (5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone (168773-45-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h

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

3: 93 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 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

upstream raw materials:

(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(hydroxymethyl)-2-piperidinone

benzyl bromide

tert-butyldimethylsilyl chloride

(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone

Downstream raw materials:

(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one

(1R,4S)-2-Benzyl-2-azabicyclo<2.2.1>-5-hepten-3-one

(1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane

Refernces