(2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester
CAS No.:1026201-47-7
Molecular Formula:C₁₉H₂₆N₂O₂
Molecular Weight:314.428
Hs Code.:

Synonyms:(2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester

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Chemical Property of (2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester

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Technology Process of (2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester

There total 7 articles about (2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl 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:

: 916914-95-9
methyl (2S,5S,6S)-6-(4-bromophenyl)-5-methylpiperidine-2-carboxylate

: 7223-38-3
N,N-Dimethylpropargylamin

: 1026201-47-7
(2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester

Guidance literature:: With copper(l) iodide; triethylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 90 ℃; for 15h;
DOI:10.1021/jo061758p

Reference yield:

: 916914-40-4
methyl (2S,5S,6S)-6-(4-bromophenyl)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-5-methylpyridine-2-carboxylate

: 1026201-47-7
(2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: H₂ / PtO₂ / ethyl acetate / 20 °C

2: 675 mg / NaBH₄ / methanol / 0.67 h / 0 °C

3: CuI; PPh₃; Et₃N / Pd(PPh₃)4 / dimethylformamide / 15 h / 90 °C

With sodium tetrahydroborate; copper(l) iodide; hydrogen; triethylamine; triphenylphosphine; platinum(IV) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; ethyl acetate; N,N-dimethyl-formamide; 3: Sonogashira reaction;
DOI:10.1021/jo061758p

Reference yield:

: (E)-(2R,3S)-2-{[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-amino}-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester

: 1026201-47-7
(2S,5S,6S)-6-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-5-methyl-piperidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: Sc(OTf)3; trifluoroacetic anhydride / CH₂Cl₂ / 20 °C

1.2: pyridine / CH₂Cl₂ / -78 - 20 °C

2.1: H₂ / PtO₂ / ethyl acetate / 20 °C

3.1: 675 mg / NaBH₄ / methanol / 0.67 h / 0 °C

4.1: CuI; PPh₃; Et₃N / Pd(PPh₃)4 / dimethylformamide / 15 h / 90 °C

With sodium tetrahydroborate; copper(l) iodide; hydrogen; triethylamine; triphenylphosphine; trifluoroacetic anhydride; scandium tris(trifluoromethanesulfonate); platinum(IV) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 4.1: Sonogashira reaction;
DOI:10.1021/jo061758p