(1S,2R)-2-[(1S)-6-methyl-1-[(1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylic acid

Base Information

Chemical Name:(1S,2R)-2-[(1S)-6-methyl-1-[(1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylic acid
CAS No.:1607007-43-1
Molecular Formula:C₂₇H₃₀N₂O₄
Molecular Weight:446.546
Hs Code.:

(1S,2R)-2-[(1S)-6-methyl-1-[(1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylic acid

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Chemical Property of (1S,2R)-2-[(1S)-6-methyl-1-[(1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylic acid

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Technology Process of (1S,2R)-2-[(1S)-6-methyl-1-[(1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylic acid

There total 13 articles about (1S,2R)-2-[(1S)-6-methyl-1-[(1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylic acid 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: 54.0%

: 1607007-41-9
benzyl(1S,2R)-2-[(1S)-6-methyl-1-[(1-oxoisoindolin-2-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]cyclohexanecarboxylate

: 1607007-43-1
(1S,2R)-2-[(1S)-6-methyl-1-[(1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylic acid

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; for 12h;
DOI:10.1002/cmdc.201300525

Reference yield:

: 13227-01-5
2-amino-2-(4-methylphenyl)acetic acid

: 1607007-43-1
(1S,2R)-2-[(1S)-6-methyl-1-[(1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 19 h / Cooling with ice; Reflux

2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Cooling with ice

3.1: potassium carbonate / N,N-dimethyl-formamide / 56 h / 20 - 40 °C

4.1: sodium hydroxide / tetrahydrofuran / 2 h / 20 °C

5.1: aluminum (III) chloride; thionyl chloride / dichloromethane; N,N-dimethyl-formamide / Cooling with ice

6.1: palladium 10% on activated carbon; hydrogen / ethanol / 72 h / 20 °C

7.1: sodium hydroxide / ethanol / 10 h / Reflux

8.1: 1H-imidazole; triethylamine; thionyl chloride / dichloromethane / 1 h / 0 °C

8.2: 1.5 h / 0 °C

9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2.5 h / 20 °C

10.1: Chiralpak AD / ethanol; methanol / Resolution of racemate

11.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C

12.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 12 h

With 1H-imidazole; aluminum (III) chloride; lithium aluminium tetrahydride; thionyl chloride; palladium 10% on activated carbon; hydrogen; sodium hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/cmdc.201300525

Reference yield:

: 2-[[6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]isoindolin-1-one

: 1607007-43-1
(1S,2R)-2-[(1S)-6-methyl-1-[(1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]cyclohexane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: Chiralpak AD / ethanol; methanol / Resolution of racemate

2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C

3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 12 h

With palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;
DOI:10.1002/cmdc.201300525