1(2H)-Pyridinecarboxylic acid, 5,6-dihydro-5-hydroxy-2-(1H-indol-3-yl)-3-(2-methyl-1,3-dioxolan-2-yl)-, phenylmethyl ester, trans-

Base Information

• Chemical Name: 1(2H)-Pyridinecarboxylic acid, 5,6-dihydro-5-hydroxy-2-(1H-indol-3-yl)-3-(2-methyl-1,3-dioxolan-2-yl)-, phenylmethyl ester, trans-
• CAS No.: 93264-59-6
• Molecular Formula: C₂₅H₂₆N₂O₅
• Molecular Weight: 434.492
• Mol file: 93264-59-6.mol

Synonyms:

Chemical Property of 1(2H)-Pyridinecarboxylic acid, 5,6-dihydro-5-hydroxy-2-(1H-indol-3-yl)-3-(2-methyl-1,3-dioxolan-2-yl)-, phenylmethyl ester, trans-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1(2H)-Pyridinecarboxylic acid, 5,6-dihydro-5-hydroxy-2-(1H-indol-3-yl)-3-(2-methyl-1,3-dioxolan-2-yl)-, phenylmethyl ester, trans-

There total 5 articles about 1(2H)-Pyridinecarboxylic acid, 5,6-dihydro-5-hydroxy-2-(1H-indol-3-yl)-3-(2-methyl-1,3-dioxolan-2-yl)-, phenylmethyl ester, trans- 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:

3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (55676-25-0) → (3R,6R)-3-Hydroxy-6-(1H-indol-3-yl)-5-(2-methyl-[1,3]dioxolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester (93264-59-6,102349-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / NaAl(MeOCH₂CH₂O)2H₂ / tetrahydrofuran / 0.5 h / -70 °C

2: 1.) O₂, methylene blue; 2.) SnCl₂ / 1.) CH₂Cl₂, -60 deg C, 30 min, irradiation; 2.) EtOAc, -60 deg C -> 5 deg C, 2h

With oxygen; methylene blue; sodium bis(2-methoxyethoxy)aluminium dihydride; tin(ll) chloride; In tetrahydrofuran;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (3R,6R)-3-Hydroxy-6-(1H-indol-3-yl)-5-(2-methyl-[1,3]dioxolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester (93264-59-6,102349-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / NaAl(MeOCH₂CH₂O)2H₂ / tetrahydrofuran / 0.5 h / -70 °C

2: 1.) O₂, methylene blue; 2.) SnCl₂ / 1.) CH₂Cl₂, -60 deg C, 30 min, irradiation; 2.) EtOAc, -60 deg C -> 5 deg C, 2h

With oxygen; methylene blue; sodium bis(2-methoxyethoxy)aluminium dihydride; tin(ll) chloride; In tetrahydrofuran;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (3R,6R)-3-Hydroxy-6-(1H-indol-3-yl)-5-(2-methyl-[1,3]dioxolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester (93264-59-6,102349-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) 70percent NaAl(MeOCH₂CH₂O)2H₂ / 1.) THF, toluene, -70 deg C, 30 min, 2.) THF,toluene, -70 deg C, 30 min

2: 1.) O₂, 2.) SnCl₂ / 1.) methylene blue, CH₂Cl₂, -60 deg C, 30 min, irradiation, 2.) CH₂Cl₂, EtOAc, -60 deg C, 10 min, then -5 deg C, 2 h

With oxygen; sodium bis(2-methoxyethoxy)aluminium dihydride; tin(ll) chloride;

DOI:10.1016/S0040-4020(01)96582-2

upstream raw materials:

indole

5-(2-Methyl-[1,3]dioxolan-2-yl)-2H-pyridine-1-carboxylic acid benzyl ester

3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine

benzyl chloroformate

Downstream raw materials:

(2S,3S)-3-Acetyl-2-(1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester

(2S,3R,5R)-3-Acetyl-2-(1H-indol-3-yl)-5-(2-methoxy-ethoxymethoxy)-piperidine-1-carboxylic acid benzyl ester

(2S,3R,5R)-3-Acetyl-5-benzoyloxy-2-(1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester

(2S,3R,5R)-3-Acetyl-5-(1-ethoxy-ethoxy)-2-(1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester