(6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]piperidin-2-one

Base Information

• Chemical Name: (6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]piperidin-2-one
• CAS No.: 209257-75-0
• Molecular Formula: C22H29NO2Si
• Molecular Weight: 367.563
• DSSTox Substance ID: DTXSID20470564
• Nikkaji Number: J1.732.853K
• Wikidata: Q82298694
• Mol file: 209257-75-0.mol

Synonyms:209257-75-0;(6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]piperidin-2-one;SCHEMBL15348613;DTXSID20470564

Chemical Property of (6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]piperidin-2-one

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 367.196755702
• Heavy Atom Count: 26
• Complexity: 443

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OCC3CCCC(=O)N3
• Isomeric SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OC[C@@H]3CCCC(=O)N3

Technology Process of (6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]piperidin-2-one

There total 10 articles about (6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]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: 94.0%

(+)-(S)-6-hydroxymethyl-2-piperidinone (128726-47-6) + tert-butylchlorodiphenylsilane (58479-61-1) → (S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one (209257-75-0)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1021/acs.jmedchem.9b00790

Reference yield: 84.0%

(S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-hexanoic acid 4-methoxy-benzyl ester (213533-01-8) → (S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one (209257-75-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 18h; under 760 Torr; Ambient temperature;

DOI:10.1055/s-1998-2123

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one (209257-75-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 95 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: 83 percent / NaN₃ / dimethylformamide / 18 h / 80 °C

4: 84 percent / H₂ / Pd/C / ethanol / 18 h / 760 Torr / Ambient temperature

With 1H-imidazole; sodium azide; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1998-2123

upstream raw materials:

(+)-(S)-6-hydroxymethyl-2-piperidinone

tert-butylchlorodiphenylsilane

(S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-hexanoic acid 4-methoxy-benzyl ester

(4-methoxyphenyl)methyl hex-5-enoate

Downstream raw materials:

2-(tert-butyl-diphenylsilanyloxymethyl)-6-oxo-piperidine-1-carboxylic acid tert-butyl ester

(+)-(S)-6-hydroxymethyl-2-piperidinone

(S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-piperidine-2-thione

3-(tert-butyl-diphenylsilanyloxymethyl)-2-aza-bicyclo[4.1.0]heptane-2-carboxylic acid tert-butyl ester