(2S,3S,4R,5S)-N-methyl-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Base Information

Chemical Name:(2S,3S,4R,5S)-N-methyl-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol
CAS No.:1301240-43-6
Molecular Formula:C₁₆H₂₃NO₃
Molecular Weight:277.364
Hs Code.:

Synonyms:(2S,3S,4R,5S)-N-methyl-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

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Chemical Property of (2S,3S,4R,5S)-N-methyl-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

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Technology Process of (2S,3S,4R,5S)-N-methyl-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

There total 9 articles about (2S,3S,4R,5S)-N-methyl-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol 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: 40.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 1301240-42-5
C₁₅H₂₁NO₃

: 1301240-35-6
4-epi-(+)-codonopsinine

: 1301240-43-6
(2S,3S,4R,5S)-N-methyl-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Guidance literature:: With formic acid; In water; at 80 ℃; Inert atmosphere;
DOI:10.1021/jo200176u

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 1301240-35-6
4-epi-(+)-codonopsinine

: 1301240-43-6
(2S,3S,4R,5S)-N-methyl-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine / 16 h / 20 °C / Inert atmosphere

2: sodium iodide / 1,4-dioxane; N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere

3: palladium on carbon; hydrogen; triethylamine / ethanol / 760.05 Torr

4: dichloromethane / 24 h / 20 °C / Molecular sieve; Inert atmosphere

5: tetrahydrofuran / 7 h / 20 °C / Inert atmosphere

6: pyridine; methanesulfonyl chloride / 16 h / 20 °C / Inert atmosphere

7: palladium on carbon; hydrogen / methanol / 48 h

8: formic acid / water / 80 °C / Inert atmosphere

With pyridine; formic acid; palladium on carbon; hydrogen; methanesulfonyl chloride; triethylamine; sodium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 8: Eschweiler-Clarke reaction;
DOI:10.1021/jo200176u

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-Ribose

: 1301240-35-6
4-epi-(+)-codonopsinine

: 1301240-43-6
(2S,3S,4R,5S)-N-methyl-2-[4-methoxyphenyl]-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Guidance literature:: Multi-step reaction with 9 steps

1: sulfuric acid / Inert atmosphere

2: pyridine / 16 h / 20 °C / Inert atmosphere

3: sodium iodide / 1,4-dioxane; N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere

4: palladium on carbon; hydrogen; triethylamine / ethanol / 760.05 Torr

5: dichloromethane / 24 h / 20 °C / Molecular sieve; Inert atmosphere

6: tetrahydrofuran / 7 h / 20 °C / Inert atmosphere

7: pyridine; methanesulfonyl chloride / 16 h / 20 °C / Inert atmosphere

8: palladium on carbon; hydrogen / methanol / 48 h

9: formic acid / water / 80 °C / Inert atmosphere

With pyridine; formic acid; sulfuric acid; palladium on carbon; hydrogen; methanesulfonyl chloride; triethylamine; sodium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 9: Eschweiler-Clarke reaction;
DOI:10.1021/jo200176u