tert-butyl (5R,7S)-2,2-dimethyl-7-{1-methyl-5-[5-(4-methylphenyl)pentanoyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro[4.4]nonane-1-carboxylate

Base Information

• Chemical Name: tert-butyl (5R,7S)-2,2-dimethyl-7-{1-methyl-5-[5-(4-methylphenyl)pentanoyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro[4.4]nonane-1-carboxylate
• CAS No.: 1431329-93-9
• Molecular Formula: C₃₁H₄₄N₂O₄
• Molecular Weight: 508.701
• Mol file: 1431329-93-9.mol

Synonyms:tert-butyl (5R,7S)-2,2-dimethyl-7-{1-methyl-5-[5-(4-methylphenyl)pentanoyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro[4.4]nonane-1-carboxylate

Chemical Property of tert-butyl (5R,7S)-2,2-dimethyl-7-{1-methyl-5-[5-(4-methylphenyl)pentanoyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro[4.4]nonane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (5R,7S)-2,2-dimethyl-7-{1-methyl-5-[5-(4-methylphenyl)pentanoyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro[4.4]nonane-1-carboxylate

There total 21 articles about tert-butyl (5R,7S)-2,2-dimethyl-7-{1-methyl-5-[5-(4-methylphenyl)pentanoyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro[4.4]nonane-1-carboxylate 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:

C43H58N2O5 (1431329-92-8) → tert-butyl (5R,7S)-2,2-dimethyl-7-{1-methyl-5-[5-(4-methylphenyl)pentanoyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro[4.4]nonane-1-carboxylate (1431329-93-9)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; methanol; at 60 ℃; for 2h;

DOI:10.1016/j.tetasy.2013.02.015

Reference yield:

3-(((tert-butyldimethylsilyl)oxy)methyl)cyclopent-2-en-1-one (140840-85-3) → tert-butyl (5R,7S)-2,2-dimethyl-7-{1-methyl-5-[5-(4-methylphenyl)pentanoyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro[4.4]nonane-1-carboxylate (1431329-93-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: (S)-DTBM-SEGPHOS; copper(II) acetate monohydrate / toluene / 3 h / 20 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

2.2: 1 h / -78 - 0 °C

3.1: dichloromethane / 0.5 h / 0 °C

4.1: water; potassium carbonate / 2 h / 0 - 20 °C

5.1: [bis(acetoxy)iodo]benzene; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; magnesium oxide / benzene / 1 h / 60 °C

6.1: triethylamine; dmap / dichloromethane / 1 h / 20 °C

7.1: methanol; potassium carbonate / tetrahydrofuran / 2.25 h / 20 °C

8.1: boron trifluoride diethyl etherate / dichloromethane / 0.75 h / 0 - 20 °C

9.1: water; sodium hydroxide / 1,4-dioxane / 48 h / Reflux

10.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.42 h / -78 °C

10.2: 1.42 h / -78 - 20 °C

11.1: 1-methyl-1H-imidazole / toluene; acetonitrile / 17 h / 80 °C

12.1: water; sodium hydroxide / tetrahydrofuran; methanol / 2 h / 60 °C

With 1-methyl-1H-imidazole; methanol; dmap; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; (S)-DTBM-SEGPHOS; water; sodium hexamethyldisilazane; copper(II) acetate monohydrate; magnesium oxide; potassium hexamethylsilazane; potassium carbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1016/j.tetasy.2013.02.015

Reference yield:

1-benzenesulfonyl-cyclopent-3-enecarboxylic ethyl ester (1322546-74-6) → tert-butyl (5R,7S)-2,2-dimethyl-7-{1-methyl-5-[5-(4-methylphenyl)pentanoyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro[4.4]nonane-1-carboxylate (1431329-93-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 20 °C

3.1: borane-THF / tetrahydrofuran / 1.42 h / 0 °C

3.2: 1 h / 0 °C

4.1: sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite / water; dichloromethane / 1 h / 0 °C

5.1: triethylamine / tetrahydrofuran / 2 h / 50 °C

6.1: (S)-DTBM-SEGPHOS; copper(II) acetate monohydrate / toluene / 3 h / 20 °C / Inert atmosphere

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

7.2: 1 h / -78 - 0 °C

8.1: dichloromethane / 0.5 h / 0 °C

9.1: water; potassium carbonate / 2 h / 0 - 20 °C

10.1: [bis(acetoxy)iodo]benzene; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; magnesium oxide / benzene / 1 h / 60 °C

11.1: triethylamine; dmap / dichloromethane / 1 h / 20 °C

12.1: methanol; potassium carbonate / tetrahydrofuran / 2.25 h / 20 °C

13.1: boron trifluoride diethyl etherate / dichloromethane / 0.75 h / 0 - 20 °C

14.1: water; sodium hydroxide / 1,4-dioxane / 48 h / Reflux

15.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.42 h / -78 °C

15.2: 1.42 h / -78 - 20 °C

16.1: 1-methyl-1H-imidazole / toluene; acetonitrile / 17 h / 80 °C

17.1: water; sodium hydroxide / tetrahydrofuran; methanol / 2 h / 60 °C

With 1H-imidazole; 1-methyl-1H-imidazole; methanol; dmap; sodium hypochlorite; lithium aluminium tetrahydride; borane-THF; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; (S)-DTBM-SEGPHOS; water; sodium hexamethyldisilazane; copper(II) acetate monohydrate; magnesium oxide; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; triethylamine; potassium bromide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1016/j.tetasy.2013.02.015

upstream raw materials:

C₁₈H₂₈N₂O₃

C₄₃H₅₈N₂O₅

tert-butyl(dimethyl){[1-(phenylsulfonyl)cyclopent-3-en-1-yl]methoxy}silane

3-(((tert-butyldimethylsilyl)oxy)methyl)cyclopent-2-en-1-one

Downstream raw materials:

1-{5-[(1S,3R)-3-amino-3-(hydroxymethyl)cyclopentyl]-1-methyl-1H-pyrrol-2-yl}-5-(4-methylphenyl)pentan-1-one