(5R,7S)-1-(3-fluorophenyl)-8-(3-isopropoxybenzyl)-7-meth-yl-1,8-diazaspiro[4.5]dec-3-en-2-one

Base Information

• Chemical Name: (5R,7S)-1-(3-fluorophenyl)-8-(3-isopropoxybenzyl)-7-meth-yl-1,8-diazaspiro[4.5]dec-3-en-2-one
• CAS No.: 1426254-45-6
• Molecular Formula: C₂₅H₂₉FN₂O₂
• Molecular Weight: 408.516

Synonyms:(5R,7S)-1-(3-fluorophenyl)-8-(3-isopropoxybenzyl)-7-meth-yl-1,8-diazaspiro[4.5]dec-3-en-2-one

Chemical Property of (5R,7S)-1-(3-fluorophenyl)-8-(3-isopropoxybenzyl)-7-meth-yl-1,8-diazaspiro[4.5]dec-3-en-2-one

Chemical Property:

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Technology Process of (5R,7S)-1-(3-fluorophenyl)-8-(3-isopropoxybenzyl)-7-meth-yl-1,8-diazaspiro[4.5]dec-3-en-2-one

There total 17 articles about (5R,7S)-1-(3-fluorophenyl)-8-(3-isopropoxybenzyl)-7-meth-yl-1,8-diazaspiro[4.5]dec-3-en-2-one 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: 87.0%

1-(bromomethyl)-3-isopropoxybenzene (184970-27-2) + (5R,7S)-1-(3-fluorophenyl)-7-methyl-1,8-diazaspiro[4.5]dec-3-en-2-one (1227685-15-5) → (5R,7S)-1-(3-fluorophenyl)-8-(3-isopropoxybenzyl)-7-meth-yl-1,8-diazaspiro[4.5]dec-3-en-2-one (1426254-45-6)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jo400016m

Reference yield:

benzyl (2S)-2-methyl-4-oxopiperidine-1-carboxylate (921599-74-8,852051-10-6) → (5R,7S)-1-(3-fluorophenyl)-8-(3-isopropoxybenzyl)-7-meth-yl-1,8-diazaspiro[4.5]dec-3-en-2-one (1426254-45-6)

Guidance literature:

Multi-step reaction with 10 steps

1: magnesium chloride; lithium hexamethyldisilazane / 1,2-dimethoxyethane / 4 h / -78 - -20 °C / Inert atmosphere

2: 18-crown-6 ether; sodium azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C / Inert atmosphere; Cooling with ice

3: zinc; acetic acid / tetrahydrofuran / 20 h / 20 - 50 °C

4: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C / Inert atmosphere

5: sodium ethanolate / ethanol / 0.5 h / 20 °C / Inert atmosphere

6: sodium tetrahydroborate / methanol / 1.5 h / 25 °C / Inert atmosphere

7: triethylamine; methanesulfonyl chloride / dichloromethane / 3 h / 20 °C / Inert atmosphere

8: potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine / 1,4-dioxane / 90 °C / Inert atmosphere

9: hydrogenchloride / water; methanol / 6 h / 90 °C / Inert atmosphere

10: potassium carbonate / acetonitrile / 18 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; potassium phosphate; copper(l) iodide; sodium azide; 18-crown-6 ether; sodium ethanolate; potassium carbonate; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; magnesium chloride; lithium hexamethyldisilazane; N,N`-dimethylethylenediamine; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetonitrile; 5: |Dieckmann Condensation / 8: |Goldberg Reaction;

DOI:10.1021/jo400016m

Reference yield:

benzyl (2S,4S)-4-hydroxy-2-methyl-4-(trichloromethyl)-piperidine-1-carboxylate (1227685-18-8) → (5R,7S)-1-(3-fluorophenyl)-8-(3-isopropoxybenzyl)-7-meth-yl-1,8-diazaspiro[4.5]dec-3-en-2-one (1426254-45-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 18-crown-6 ether; sodium azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C / Inert atmosphere; Cooling with ice

2: zinc; acetic acid / tetrahydrofuran / 20 h / 20 - 50 °C

3: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C / Inert atmosphere

4: sodium ethanolate / ethanol / 0.5 h / 20 °C / Inert atmosphere

5: acetic acid / water; 1,4-dioxane / 1 h / Inert atmosphere; Reflux

6: sodium tetrahydroborate / methanol / 1.5 h / 25 °C / Inert atmosphere

7: triethylamine; methanesulfonyl chloride / dichloromethane / 3 h / 20 °C / Inert atmosphere

8: potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine / 1,4-dioxane / 90 °C / Inert atmosphere

9: hydrogenchloride / water; methanol / 6 h / 90 °C / Inert atmosphere

10: potassium carbonate / acetonitrile / 18 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; potassium phosphate; copper(l) iodide; sodium azide; 18-crown-6 ether; sodium ethanolate; potassium carbonate; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N`-dimethylethylenediamine; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetonitrile; 4: |Dieckmann Condensation / 8: |Goldberg Reaction;

DOI:10.1021/jo400016m

upstream raw materials:

8-benzyl 3-ethyl (5R,7S)-4-amino-1-(3-fluorophenyl)-7-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-ene-3,8-dicarboxylate

C₁₅H₁₇FN₂O₂

benzyl (2S,4R)-4-cyano-4-[(3-ethoxy-3-oxopropanoyl)(3-fluorophenyl)amino]-2-methylpiperidine-1-carboxylate

benzyl 1-(3-fluorophenyl)-4-hydroxy-7-methyl-2-oxo-1,8-diazaspiro[4.5]decane-8-carboxylate

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