[(1S,3S)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl]methanol

Base Information

Chemical Name:[(1S,3S)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl]methanol
CAS No.:1322547-96-5
Molecular Formula:C₁₇H₂₁NO₃S
Molecular Weight:319.425
Hs Code.:

Synonyms:[(1S,3S)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl]methanol

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Chemical Property of [(1S,3S)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl]methanol

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Technology Process of [(1S,3S)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl]methanol

There total 7 articles about [(1S,3S)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl]methanol 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:

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 1218790-43-2
1-(p-toluenesulfonyl)pyrrole-2-boronic acid pinacol ester

: (3S)-3-(tert-butyldimethylsilyloxy)methylcyclopentan-1-one

: 1322547-96-5
[(1S,3S)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl]methanol

: 1431329-95-1
[(1S,3R)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl]methanol

Guidance literature:: (3S)-3-(tert-butyldimethylsilyloxy)methylcyclopentan-1-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

N,N-phenylbistrifluoromethane-sulfonimide; In tetrahydrofuran; at -78 - 0 ℃; for 1h;

1-(p-toluenesulfonyl)pyrrole-2-boronic acid pinacol ester; Overall yield = 95 %; Overall yield = 15.6 g; Further stages;
DOI:10.1016/j.tetasy.2013.02.015

Reference yield:

: 140840-85-3
3-(((tert-butyldimethylsilyl)oxy)methyl)cyclopent-2-en-1-one

: 1322547-96-5
[(1S,3S)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl]methanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; copper(l) chloride; sodium t-butanolate / 91 h / 0 - 20 °C

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

2.2: 1 h / -78 - 0 °C

With sodium hexamethyldisilazane; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran;
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

: 1322547-96-5
[(1S,3S)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl]methanol

Guidance literature:: Multi-step reaction with 5 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

With sodium hypochlorite; borane-THF; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (S)-DTBM-SEGPHOS; sodium hexamethyldisilazane; copper(II) acetate monohydrate; sodium hydrogencarbonate; triethylamine; potassium bromide; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1016/j.tetasy.2013.02.015