2-[2-hydroxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pirrolidin-3-yl]-ethanol

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Chemical Name:2-[2-hydroxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pirrolidin-3-yl]-ethanol
CAS No.:536745-01-4
Molecular Formula:C₁₇H₂₅NO₄S
Molecular Weight:339.456
Hs Code.:

Synonyms:2-[2-hydroxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pirrolidin-3-yl]-ethanol

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Chemical Property of 2-[2-hydroxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pirrolidin-3-yl]-ethanol

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Technology Process of 2-[2-hydroxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pirrolidin-3-yl]-ethanol

There total 13 articles about 2-[2-hydroxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pirrolidin-3-yl]-ethanol 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%

: 536745-00-3
2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol

: 536745-01-4
2-[2-hydroxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pirrolidin-3-yl]-ethanol

Guidance literature:: 2-[(3S,4R,5R)-4-[2-(Dimethyl-phenyl-silanyl)-ethyl]-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1-trimethylsilanyl-propan-2-ol; With hydrogen fluoride; In water; acetonitrile; at 20 ℃; for 1h;

With tert.-butylhydroperoxide; potassium hydride; In decane; N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; decane; N,N-dimethyl-formamide; at 65 ℃; for 4h;
DOI:10.1021/ol034241y

Reference yield:

: 286376-23-6
4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide

: 536745-01-4
2-[2-hydroxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pirrolidin-3-yl]-ethanol

Guidance literature:: Multi-step reaction with 8 steps

1.1: Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 48 h / 20 °C

2.1: 80 percent / malonic acid; CpRu[(CH₃CN)3]PF₆ / H₂O; acetone / 3 h / 40 °C

3.1: Li / tetrahydrofuran / 4.5 h / 0 °C

3.2: CuCN / tetrahydrofuran / 0.42 h / 0 °C

3.3: 0.82 g / tetrahydrofuran / 5 h / -78 - 0 °C

4.1: 87 percent / DBU / benzene / 7 h / Heating

5.1: 93 percent / formic acid; Pd/C / methanol / 4 h / 20 °C

6.1: 65 percent / B(O-iPr)3; H₂ / Ir(cod)Py(PCy₃)PF₆ / CH₂Cl₂ / 24 h / 103430 Torr

7.1: 65 percent / tetrahydrofuran; pentane / 5 h / -78 °C

8.1: aq. HF / acetonitrile / 1 h

8.2: KH; t-butyl hydroperoxide / dimethylformamide / 0.17 h / 20 °C

8.3: 90 percent / TBAF / tetrahydrofuran; dimethylformamide / 4 h / 65 °C

With palladium on activated charcoal; formic acid; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; Triisopropyl borate; malonic acid; di-isopropyl azodicarboxylate; hydrogen fluoride; hydrogen; lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; Crabtree's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; pentane; benzene; 1.1: Mitsunobu reaction;
DOI:10.1021/ja043097o

Reference yield:

: 536744-93-1
1-benzyloxy-5-(tert-butyldimethylsilanoxy)pent-3-yn-2-one

: 536745-01-4
2-[2-hydroxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pirrolidin-3-yl]-ethanol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / LiAlH₄; MeOH; (R)-BINOL / tetrahydrofuran / 0.5 h / -100 - -78 °C

2.1: Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 48 h / 20 °C

3.1: 80 percent / malonic acid; CpRu[(CH₃CN)3]PF₆ / H₂O; acetone / 3 h / 40 °C

4.1: Li / tetrahydrofuran / 4.5 h / 0 °C

4.2: CuCN / tetrahydrofuran / 0.42 h / 0 °C

4.3: 0.82 g / tetrahydrofuran / 5 h / -78 - 0 °C

5.1: 87 percent / DBU / benzene / 7 h / Heating

6.1: 93 percent / formic acid; Pd/C / methanol / 4 h / 20 °C

7.1: 65 percent / B(O-iPr)3; H₂ / Ir(cod)Py(PCy₃)PF₆ / CH₂Cl₂ / 24 h / 103430 Torr

8.1: 65 percent / tetrahydrofuran; pentane / 5 h / -78 °C

9.1: aq. HF / acetonitrile / 1 h

9.2: KH; t-butyl hydroperoxide / dimethylformamide / 0.17 h / 20 °C

9.3: 90 percent / TBAF / tetrahydrofuran; dimethylformamide / 4 h / 65 °C

With methanol; palladium on activated charcoal; lithium aluminium tetrahydride; formic acid; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; Triisopropyl borate; malonic acid; di-isopropyl azodicarboxylate; hydrogen fluoride; hydrogen; (R)-1,1'-Bi-2-naphthol; lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; Crabtree's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; pentane; benzene; 2.1: Mitsunobu reaction;
DOI:10.1021/ja043097o