(2S,6S)-2-[(1E,3Z)-(S)-5-((E)-3-Cyclohex-1-enyl-acryloyloxy)-hexa-1,3-dienyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,6S)-2-[(1E,3Z)-(S)-5-((E)-3-Cyclohex-1-enyl-acryloyloxy)-hexa-1,3-dienyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester
CAS No.:344335-56-4
Molecular Formula:C₂₆H₃₉NO₄
Molecular Weight:429.6
Hs Code.:

Synonyms:(2S,6S)-2-[(1E,3Z)-(S)-5-((E)-3-Cyclohex-1-enyl-acryloyloxy)-hexa-1,3-dienyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,6S)-2-[(1E,3Z)-(S)-5-((E)-3-Cyclohex-1-enyl-acryloyloxy)-hexa-1,3-dienyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,6S)-2-[(1E,3Z)-(S)-5-((E)-3-Cyclohex-1-enyl-acryloyloxy)-hexa-1,3-dienyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

There total 6 articles about (2S,6S)-2-[(1E,3Z)-(S)-5-((E)-3-Cyclohex-1-enyl-acryloyloxy)-hexa-1,3-dienyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester 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: 83.0%

: 56453-88-4
(E)-3-(1-cyclohexen-1-yl)-2-propenoic acid

: 344335-60-0
(2S,6S)-2-((1E,3Z)-(S)-5-Hydroxy-hexa-1,3-dienyl)-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

: 344335-56-4
(2S,6S)-2-[(1E,3Z)-(S)-5-((E)-3-Cyclohex-1-enyl-acryloyloxy)-hexa-1,3-dienyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;
DOI:10.1021/ol010038w

Reference yield:

: 168610-13-7
1,1-dimethyl<(2R,6S)-2-formyl-6-methyl-1-piperidine>carboxylate

: 344335-56-4
(2S,6S)-2-[(1E,3Z)-(S)-5-((E)-3-Cyclohex-1-enyl-acryloyloxy)-hexa-1,3-dienyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / silica gel; Et₃N / ethyl acetate; hexane / 22 h

2: 63 percent / CrCl₂ / tetrahydrofuran

3: 73 percent / CuI; piperidine / PdCl₂(PhCN)2 / tetrahydrofuran / 20 °C

4: 100 percent / H₂; quinoline / Lindlar / methanol; CH₂Cl₂

5: 83 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; DMAP; TEMPO / CH₂Cl₂

With piperidine; quinoline; chromium dichloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(l) iodide; hydrogen; silica gel; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; Lindlar's catalyst; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; 3: Sonogashira coupling;
DOI:10.1021/ol010038w

Reference yield:

: 183903-99-3
(+)-(S)-N-tert-butoxycarbonyl-2-methylpiperidine

: 344335-56-4
(2S,6S)-2-[(1E,3Z)-(S)-5-((E)-3-Cyclohex-1-enyl-acryloyloxy)-hexa-1,3-dienyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / sec-BuLi; TMEDA / diethyl ether / -78 °C

2: 83 percent / silica gel; Et₃N / ethyl acetate; hexane / 22 h

3: 63 percent / CrCl₂ / tetrahydrofuran

4: 73 percent / CuI; piperidine / PdCl₂(PhCN)2 / tetrahydrofuran / 20 °C

5: 100 percent / H₂; quinoline / Lindlar / methanol; CH₂Cl₂

6: 83 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; DMAP; TEMPO / CH₂Cl₂

With piperidine; quinoline; chromium dichloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; hydrogen; sec.-butyllithium; silica gel; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; Lindlar's catalyst; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; 4: Sonogashira coupling;
DOI:10.1021/ol010038w