methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate

Base Information

• Chemical Name: methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate
• CAS No.: 442202-20-2
• Molecular Formula: C₂₄H₃₁NO₄Si
• Molecular Weight: 425.6
• Mol file: 442202-20-2.mol

Synonyms:methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate

Chemical Property of methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate

There total 1 articles about methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate 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: 98.0%

methyl chloroformate (79-22-1) + (S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one (209257-75-0) → methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate (442202-20-2)

Guidance literature:

(S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

methyl chloroformate; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 2h;

DOI:10.1016/j.tet.2004.05.039

Reference yield: 96.0%

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide (145100-51-2) + methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate (442202-20-2) → methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylate (442202-21-3)

Guidance literature:

methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide; In tetrahydrofuran; hexane; at -78 - -40 ℃; for 1h;

DOI:10.1016/j.tet.2004.05.039

Reference yield:

methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate (442202-20-2) → (2S,3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-2-propyl-piperidine-1-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium hexamethyldisilazide / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 96 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

2.1: Pd(Ph₃P)4 / dimethylformamide / 0.5 h / 20 °C

2.2: 88 percent / Et₃N / dimethylformamide / 15 h / 70 °C

3.1: CuI / diethyl ether / 0.33 h / -78 - -35 °C

3.2: 96 percent / diethyl ether / 1 h / -78 - -30 °C

4.1: 96 percent / Super-Hydride / tetrahydrofuran / 1 h / 0 °C

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

6.2: 691 mg / tetrahydrofuran; hexane / 2 h / 20 °C

7.1: hydrogen / Pd-C / ethyl acetate / 48 h / 760.05 Torr

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; hydrogen; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3.2: Michael addition / 5.1: Swern oxidation;

DOI:10.1021/ol025775m

upstream raw materials:

methyl chloroformate

(S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one

Downstream raw materials:

methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylate

dimethyl (2S,3R,5R,6S)-(-)-5-ethyl-6-propyl-3-vinylpiperidine-1,2-dicarboxylate

dimethyl (S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-propenyl-3-vinylpiperidine-1-carboxylate