4-benzyloxy-5-[(3R)-3-hydroxy-3-(2-methylphenyl)propyl]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

Base Information

Chemical Name:4-benzyloxy-5-[(3R)-3-hydroxy-3-(2-methylphenyl)propyl]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide
CAS No.:1034771-28-2
Molecular Formula:C₂₉H₃₃N₃O₃
Molecular Weight:471.599
Hs Code.:

Synonyms:4-benzyloxy-5-[(3R)-3-hydroxy-3-(2-methylphenyl)propyl]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

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Chemical Property of 4-benzyloxy-5-[(3R)-3-hydroxy-3-(2-methylphenyl)propyl]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

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Technology Process of 4-benzyloxy-5-[(3R)-3-hydroxy-3-(2-methylphenyl)propyl]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

There total 7 articles about 4-benzyloxy-5-[(3R)-3-hydroxy-3-(2-methylphenyl)propyl]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide 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:

: 1034771-27-1
4-benzyloxy-N,N,1,2-tetramethyl-5-[3-(2-methylphenyl)-3-oxopropyl]-1H-benzimidazole-6-carboxamide

: 4-benzyloxy-5-((3S)-3-hydroxy-3-(2-methylphenyl)propyl)-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

: 1034771-28-2
4-benzyloxy-5-[(3R)-3-hydroxy-3-(2-methylphenyl)propyl]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

Guidance literature:: With potassium hydroxide; (R)-(+)-2-amino-1,1,2-triphenylethanol; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In water; isopropyl alcohol; at 40 ℃; for 20h; Product distribution / selectivity;

Reference yield:

: N-[2-(benzyloxy)-4-bromo-6-(dimethylamino)phenyl]acetamide

: 1034771-28-2
4-benzyloxy-5-[(3R)-3-hydroxy-3-(2-methylphenyl)propyl]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1: trichlorophosphate / 3 h / 70 - 80 °C / Inert atmosphere; Large scale

2: triphenylphosphine; palladium diacetate; dmap / tetrahydrofuran; N,N-dimethyl-formamide / 18 h / 130 °C / 3750.38 - 4500.45 Torr / Autoclave; Inert atmosphere; Large scale

3: hydrogen; 5% Pd/C / methanol / 45 - 55 °C / Inert atmosphere; Large scale

4: triethylamine; formaldehyd / isopropyl alcohol; water / 35 - 45 °C / Large scale

5: potassium 2-methylbutan-2-olate / toluene; N,N-dimethyl-formamide / 55 - 85 °C / Reflux; Large scale

6: potassium carbonate / N,N-dimethyl-formamide / 50 - 58 °C / Inert atmosphere; Large scale

7: RuCl₂[(S)-Xyl-P-Phos][(S)-DAIPEN]; potassium tert-butylate; hydrogen / isopropyl alcohol; tert-butyl alcohol / 20 h / 70 °C / 60006 Torr / Autoclave; Inert atmosphere

With dmap; formaldehyd; RuCl₂[(S)-Xyl-P-Phos][(S)-DAIPEN]; 5% Pd/C; potassium tert-butylate; hydrogen; palladium diacetate; potassium 2-methylbutan-2-olate; potassium carbonate; triethylamine; triphenylphosphine; trichlorophosphate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; tert-butyl alcohol;
DOI:10.1021/op800177x

Reference yield:

: 4-(benzyloxy)-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

: 1034771-28-2
4-benzyloxy-5-[(3R)-3-hydroxy-3-(2-methylphenyl)propyl]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1: hydrogen; 5% Pd/C / methanol / 45 - 55 °C / Inert atmosphere; Large scale

2: triethylamine; formaldehyd / isopropyl alcohol; water / 35 - 45 °C / Large scale

3: potassium 2-methylbutan-2-olate / toluene; N,N-dimethyl-formamide / 55 - 85 °C / Reflux; Large scale

4: potassium carbonate / N,N-dimethyl-formamide / 50 - 58 °C / Inert atmosphere; Large scale

5: RuCl₂[(S)-Xyl-P-Phos][(S)-DAIPEN]; potassium tert-butylate; hydrogen / isopropyl alcohol; tert-butyl alcohol / 20 h / 70 °C / 60006 Torr / Autoclave; Inert atmosphere

With formaldehyd; RuCl₂[(S)-Xyl-P-Phos][(S)-DAIPEN]; 5% Pd/C; potassium tert-butylate; hydrogen; potassium 2-methylbutan-2-olate; potassium carbonate; triethylamine; In methanol; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; tert-butyl alcohol;
DOI:10.1021/op800177x