1-[(3S,4S)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine

Base Information

Chemical Name:1-[(3S,4S)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine
CAS No.:1251908-00-5
Molecular Formula:C₂₂H₂₄N₄
Molecular Weight:344.459
Hs Code.:

Synonyms:1-[(3S,4S)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine

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Chemical Property of 1-[(3S,4S)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine

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Technology Process of 1-[(3S,4S)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine

There total 7 articles about 1-[(3S,4S)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine 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:

: (±)-cis-1-[1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine

: 1251907-99-9
1-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine

: 1251908-00-5
1-[(3S,4S)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine

Guidance literature:: With DAICEL CHIRALPAK IA; In ethanol; at 20 ℃; Purification / work up;

Reference yield:

: (±)-cis-4-{[1-benzyl-4-methylpiperidin-3-yl]amino}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

: 1251907-99-9
1-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine

: 1251908-00-5
1-[(3S,4S)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / Cooling with ice

1.2: 4 h / 20 °C

2.1: acetyl chloride / water; methanol / 5 h / 80 °C

3.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C

3.2: 20 °C

4.1: DAICEL CHIRALPAK IA / ethanol / 20 °C

With sodium hexamethyldisilazane; acetyl chloride; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

Reference yield:

: 920966-02-5
4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

: 1251908-00-5
1-[(3S,4S)-1-benzyl-4-methylpiperidin-3-yl]-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil; tetrahydrofuran / 0.33 h / 0 °C

1.2: 3 h / 0 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 2 h / 180 °C

3.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / 0 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C

4.2: 13 h / 0 - 20 °C

5.1: acetyl chloride / methanol / 0.5 h / 80 °C

6.1: trifluoroacetic acid / dichloromethane / 20 °C

6.2: 2 h / 20 °C

7.1: DAICEL CHIRALPAK IA 5 mm, 20 mm Φ X 250 mm / hexane; ethanol / Resolution of racemate

With sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil; 4.1: |Wittig Olefination / 4.2: |Wittig Olefination;
DOI:10.1016/j.bmc.2017.07.043