(2S)-(-)-4-(1-hydroxyethyl)-N-methyl-2-(N-p-toluenesulfonylindol-3-yl)-1,2,5,6-tetrahydropyridine

Base Information

Chemical Name:(2S)-(-)-4-(1-hydroxyethyl)-N-methyl-2-(N-p-toluenesulfonylindol-3-yl)-1,2,5,6-tetrahydropyridine
CAS No.:461641-27-0
Molecular Formula:C₂₃H₂₆N₂O₃S
Molecular Weight:410.537
Hs Code.:

Synonyms:(2S)-(-)-4-(1-hydroxyethyl)-N-methyl-2-(N-p-toluenesulfonylindol-3-yl)-1,2,5,6-tetrahydropyridine

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Chemical Property of (2S)-(-)-4-(1-hydroxyethyl)-N-methyl-2-(N-p-toluenesulfonylindol-3-yl)-1,2,5,6-tetrahydropyridine

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Technology Process of (2S)-(-)-4-(1-hydroxyethyl)-N-methyl-2-(N-p-toluenesulfonylindol-3-yl)-1,2,5,6-tetrahydropyridine

There total 15 articles about (2S)-(-)-4-(1-hydroxyethyl)-N-methyl-2-(N-p-toluenesulfonylindol-3-yl)-1,2,5,6-tetrahydropyridine 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: 55.0%

: 917-54-4
methyllithium

: 1-methyl-6-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-1,2,3,6-tetrahydro-pyridine-4-carbaldehyde

: 461641-27-0
(2S)-(-)-4-(1-hydroxyethyl)-N-methyl-2-(N-p-toluenesulfonylindol-3-yl)-1,2,5,6-tetrahydropyridine

Guidance literature:: In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.0833333h;
DOI:10.1021/ja026464+

Reference yield:

: (E)-1-(N-p-toluenesulfonyl-3-indolyl)-2-tributylstannylethene

: 461641-27-0
(2S)-(-)-4-(1-hydroxyethyl)-N-methyl-2-(N-p-toluenesulfonylindol-3-yl)-1,2,5,6-tetrahydropyridine

Guidance literature:: Multi-step reaction with 8 steps

1: 5.14 g / LiCl / Pd(PPh₃)4 / dimethylformamide / 0.5 h / 115 °C

2: 67 percent / MnO₂ / CH₂Cl₂ / 0.22 h / 20 °C

3: CHCl₃ / 12 h / 23 °C

4: 969 mg / LiAlH₄ / diethyl ether; tetrahydrofuran / 0 - 20 °C

5: 73 percent / MnO₂ / diethyl ether / 0.05 h / 20 °C

6: 100 percent / NaBH₃CN / acetonitrile; H₂O / 0.08 h / 20 °C

7: MnO₂ / CH₂Cl₂ / 0.08 h / 20 °C

8: 55 percent / diethyl ether; tetrahydrofuran / 0.08 h / 0 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; sodium cyanoborohydride; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja026464+

Reference yield:

: 461640-91-5
ethyl (E,E)-4-oxo-2-[(N-p-toluenesulfonylindol-3-yl)vinyl]but-2-enoate

: 461641-27-0
(2S)-(-)-4-(1-hydroxyethyl)-N-methyl-2-(N-p-toluenesulfonylindol-3-yl)-1,2,5,6-tetrahydropyridine

Guidance literature:: Multi-step reaction with 6 steps

1.1: CHCl₃ / 12 h / 23 °C

2.1: 95 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.25 h / 0 - 20 °C

3.1: MnO₂ / diethyl ether / 0.05 h / 20 °C

3.2: 73 percent / SiO₂ / methanol; CHCl₃

4.1: 100 percent / NaBH₃CN / acetonitrile; H₂O / 0.08 h / 20 °C

5.1: MnO₂ / CH₂Cl₂ / 0.08 h / 20 °C

6.1: 34 mg / diethyl ether; tetrahydrofuran / 0.08 h / 0 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; acetonitrile;
DOI:10.1021/jo049381f