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

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Chemical Name:tert-Butyl [(1R,3S)-1-(hydroxymethyl)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl] carbamate
CAS No.:1322548-00-4
Molecular Formula:C₂₂H₃₀N₂O₅S
Molecular Weight:434.557
Hs Code.:

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

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

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

There total 11 articles about tert-Butyl [(1R,3S)-1-(hydroxymethyl)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl] carbamate 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:

: 1322547-99-8
tert-butyl (5R,7S)-7-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}-2-oxo-3-oxa-1-azaspiro[4.4] nonane-1-carboxylate

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

Guidance literature:: With methanol; potassium carbonate; In tetrahydrofuran; at 20 ℃; for 2.25h;
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

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

Guidance literature:: Multi-step reaction with 10 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

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; (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:

: 1322546-74-6
1-benzenesulfonyl-cyclopent-3-enecarboxylic ethyl ester

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

Guidance literature:: Multi-step reaction with 12 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: 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; copper(l) chloride; sodium t-butanolate / 91 h / 0 - 20 °C

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

With 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; water; sodium hexamethyldisilazane; magnesium oxide; sodium hydrogencarbonate; potassium carbonate; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; triethylamine; copper(l) chloride; potassium bromide; sodium t-butanolate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.tetasy.2013.02.015