(2S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-propyl-1-(toluene-4-sulfonyl)-piperidine

Base Information

Chemical Name:(2S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-propyl-1-(toluene-4-sulfonyl)-piperidine
CAS No.:272788-21-3
Molecular Formula:C₂₁H₃₇NO₃SSi
Molecular Weight:411.681
Hs Code.:

Synonyms:(2S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-propyl-1-(toluene-4-sulfonyl)-piperidine

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Chemical Property of (2S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-propyl-1-(toluene-4-sulfonyl)-piperidine

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Technology Process of (2S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-propyl-1-(toluene-4-sulfonyl)-piperidine

There total 8 articles about (2S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-propyl-1-(toluene-4-sulfonyl)-piperidine 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: 81.0%

: N-[4-(tert-butyl-dimethyl-silanyloxy)-1-propyl-5-(2,4,6-trimethyl-phenoxy)-pentyl]-4-methyl-benzenesulfonamide

: 272788-21-3
(2S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-propyl-1-(toluene-4-sulfonyl)-piperidine

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 23h;
DOI:10.1016/S0040-4020(99)01105-9

Reference yield:

: 70-55-3
toluene-4-sulfonamide

: 272788-21-3
(2S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-propyl-1-(toluene-4-sulfonyl)-piperidine

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / Pd(PPh₃)4 / acetonitrile / 6 h / 40 °C

2: 91 percent / imidazole / dimethylformamide / 4 h / 0 - 20 °C

3: 97 percent / H₂ / PtO₂ / ethanol / 3 h / 20 °C / 760 Torr

4: 93 percent / H₂ / Pd/C / methanol / 1 h / 20 °C / 760 Torr

5: Et₃N / tetrahydrofuran / 3 h / 0 - 20 °C

6: 81 percent / K₂CO₃ / methanol / 23 h / 20 °C

With 1H-imidazole; hydrogen; potassium carbonate; triethylamine; platinum(IV) oxide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile; 1: Addition / 2: Addition / 3: Hydrogenation / 4: Hydrogenation / 5: Addition / 6: Cyclization;
DOI:10.1016/S0040-4020(99)01105-9

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 272788-21-3
(2S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-propyl-1-(toluene-4-sulfonyl)-piperidine

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / imidazole / dimethylformamide / 4 h / 0 - 20 °C

2: 97 percent / H₂ / PtO₂ / ethanol / 3 h / 20 °C / 760 Torr

3: 93 percent / H₂ / Pd/C / methanol / 1 h / 20 °C / 760 Torr

4: Et₃N / tetrahydrofuran / 3 h / 0 - 20 °C

5: 81 percent / K₂CO₃ / methanol / 23 h / 20 °C

With 1H-imidazole; hydrogen; potassium carbonate; triethylamine; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; 1: Addition / 2: Hydrogenation / 3: Hydrogenation / 4: Addition / 5: Cyclization;
DOI:10.1016/S0040-4020(99)01105-9