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

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Chemical Name:tert-Butyl(5R,7S)-2,2-dimethyl-7-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro [4.4]nonane-1-carboxylate
CAS No.:1322548-01-5
Molecular Formula:C₂₅H₃₄N₂O₅S
Molecular Weight:474.621
Hs Code.:

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

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

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

There total 12 articles about tert-Butyl(5R,7S)-2,2-dimethyl-7-{1-[(4-methylphenyl)sulfonyl]-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: 90.0%

: 1322548-00-4
tert-Butyl [(1R,3S)-1-(hydroxymethyl)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl] carbamate

: 77-76-9
2,2-dimethoxy-propane

: 1322548-01-5
tert-Butyl(5R,7S)-2,2-dimethyl-7-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro [4.4]nonane-1-carboxylate

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 0.75h;
DOI:10.1016/j.tetasy.2013.02.015

Reference yield:

: 1322546-79-1
tert-butyl(dimethyl){[1-(phenylsulfonyl)cyclopent-3-en-1-yl]methoxy}silane

: 1322548-01-5
tert-Butyl(5R,7S)-2,2-dimethyl-7-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro [4.4]nonane-1-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

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

1.2: 1 h / 0 °C

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

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

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

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

5.2: 1 h / -78 - 0 °C

6.1: dichloromethane / 0.5 h / 0 °C

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

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

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

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

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

With methanol; dmap; sodium hypochlorite; 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; sodium hydrogencarbonate; potassium carbonate; triethylamine; potassium bromide; In tetrahydrofuran; dichloromethane; water; toluene; benzene;
DOI:10.1016/j.tetasy.2013.02.015

Reference yield:

: 1322546-76-8
C₁₂H₁₄O₃S

: 1322548-01-5
tert-Butyl(5R,7S)-2,2-dimethyl-7-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}-3-oxa-1-azaspiro [4.4]nonane-1-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 20 °C

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

2.2: 1 h / 0 °C

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

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

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

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

6.2: 1 h / -78 - 0 °C

7.1: dichloromethane / 0.5 h / 0 °C

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

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

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

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

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

With 1H-imidazole; methanol; dmap; sodium hypochlorite; 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; sodium hydrogencarbonate; potassium carbonate; triethylamine; potassium bromide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/j.tetasy.2013.02.015