(1S,2R)-2-[(1S)-5-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 Name:(1S,2R)-2-[(1S)-5-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.:1607007-55-5
Molecular Formula:C₂₇H₃₀N₂O₄
Molecular Weight:446.546
Hs Code.:

Synonyms:(1S,2R)-2-[(1S)-5-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)-5-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)-5-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 7 articles about (1S,2R)-2-[(1S)-5-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: 91.0%

: 1607007-54-4
benzyl (1S,2R)-2-{(1S)-5-methyl-1-[(1-oxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl}cyclohexane-1-carboxylate

: 1607007-55-5
(1S,2R)-2-[(1S)-5-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; water; at 20 ℃; for 4.5h;
DOI:10.1002/cmdc.201300525

Reference yield:

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 1607007-55-5
(1S,2R)-2-[(1S)-5-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

1.1: quinidine / toluene / 1 h / -55 °C

1.2: 96 h / -55 °C

2.1: 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

3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water / 4.5 h / 20 °C

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; quinidine; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;
DOI:10.1002/cmdc.201300525

Reference yield:

: 55755-16-3
2-methylphenethylamine

: 1607007-55-5
(1S,2R)-2-[(1S)-5-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 6 steps

1: potassium carbonate / dichloromethane / 20 °C

2: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / 120 °C

3: caesium carbonate / N,N-dimethyl-formamide / 42 h / 20 - 70 °C

4: sodium tetrahydroborate / methanol / 2 h / 20 °C

5: 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

6: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water / 4.5 h / 20 °C

With sodium tetrahydroborate; phosphorus pentoxide; palladium 10% on activated carbon; hydrogen; potassium carbonate; caesium carbonate; 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; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; water; N,N-dimethyl-formamide; 2: |Bischler-Napieralski Reaction;
DOI:10.1002/cmdc.201300525