(5R,6S)-6-(benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-2-one

Base Information

• Chemical Name: (5R,6S)-6-(benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-2-one
• CAS No.: 1131711-61-9
• Molecular Formula: C₁₉H₃₁NO₃Si
• Molecular Weight: 349.546
• Mol file: 1131711-61-9.mol

Synonyms:(5R,6S)-6-(benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-2-one

Chemical Property of (5R,6S)-6-(benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6S)-6-(benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-2-one

There total 6 articles about (5R,6S)-6-(benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-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: 90.0%

(5R,6S)-6-(benzyloxymethyl)-5-hydroxypiperidin-2-one (1131711-60-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (5R,6S)-6-(benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-2-one (1131711-61-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 15h;

DOI:10.1016/j.tetasy.2008.12.014

Reference yield:

(RS,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one (1329450-98-7) → (5R,6S)-6-(benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-2-one (1131711-61-9)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 h

2: hydrogenchloride; methanol / 1,4-dioxane / 15 h / 20 °C

3: potassium carbonate / methanol / 20 °C

4: 1H-imidazole; dmap / N,N-dimethyl-formamide / 20 °C

With 1H-imidazole; hydrogenchloride; methanol; dmap; palladium 10% on activated carbon; hydrogen; potassium carbonate; In 1,4-dioxane; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol2020384

Reference yield:

(R)-N-[(1E)-2-(benzyloxy)ethylidene]-2-methylpropane-2-sulfinamide (393536-17-9) → (5R,6S)-6-(benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-2-one (1131711-61-9)

Guidance literature:

Multi-step reaction with 5 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 h

3: hydrogenchloride; methanol / 1,4-dioxane / 15 h / 20 °C

4: potassium carbonate / methanol / 20 °C

5: 1H-imidazole; dmap / N,N-dimethyl-formamide / 20 °C

With 1H-imidazole; hydrogenchloride; methanol; dmap; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; potassium carbonate; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Mannich reaction;

DOI:10.1021/ol2020384

upstream raw materials:

(5R,6S)-6-(benzyloxymethyl)-5-hydroxypiperidin-2-one

tert-butyldimethylsilyl chloride

(R_S,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one

(R,S)-5-[(R)-(benzyloxymethyl)(tert-butanesulfinylamino)methyl]furan-2(4H)-one

Downstream raw materials:

tert-butyl (2S,3R)-2-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-6-oxopiperidine-1-carboxylate