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[ CAS No. 13379-98-1 ]

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Chemical Structure| 13379-98-1
Chemical Structure| 13379-98-1
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Product Details of [ 13379-98-1 ]

CAS No. :13379-98-1 MDL No. :MFCD00458992
Formula : C10H15NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :OXBINBPGHTWHKS-UHFFFAOYSA-N
M.W :229.30 Pubchem ID :2180655
Synonyms :

Calculated chemistry of [ 13379-98-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 58.08
TPSA : 74.78 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 0.92
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 0.74
Log Po/w (SILICOS-IT) : 0.92
Consensus Log Po/w : 1.2

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.81
Solubility : 3.57 mg/ml ; 0.0156 mol/l
Class : Very soluble
Log S (Ali) : -2.08
Solubility : 1.92 mg/ml ; 0.00839 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.41
Solubility : 0.0896 mg/ml ; 0.000391 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 13379-98-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13379-98-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 13379-98-1 ]

[ 13379-98-1 ] Synthesis Path-Downstream   1~68

  • 2
  • [ 98-59-9 ]
  • [ 156-87-6 ]
  • [ 13379-98-1 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;
99% With triethylamine In dichloromethane at 0℃; for 17h;
99% With triethylamine In chloroform at 0 - 20℃; for 18h; Inert atmosphere;
99% With triethylamine In chloroform at 0 - 20℃; for 18h; Inert atmosphere; 1 N-(3-Hydroxypropyl)-4-methylbenzenesulfonamide (I) [00029] To a cooled (0 °C) mixture of 3-aminopropan-1-ol (1.9 mL, 24.8 mmol) and Et3N (6.9 mL, 49.6 mmol, 2.0 equiv) in chloroform (4.0 mL) was added a solution ofptoluenesulfonyl chloride (5.21 g, 14.38 mmol, 1.1 equiv) in chloroform (6.0 mL, 2.5 M overall). The mixture was allowed to slowly warm to ambient temperature and stir under inert atmosphere for 18 h. The reaction was then quenched with 5% NaHCO3, and the mixture was extracted with EtOAc (x3). The combined organic layers were washed successively with 5% citric acid, water, 5% NaHCO3, and brine. Then the organic layers were dried over Mg504, filtered, and concentrated in vacuo to provide N-(3-hydroxypropyl)-4-methylbenzenesulfonamide (5.70 g, 24.8 mmol, 99% yield). Carried on to next step without further purification.[00030] Analytical data for I: ‘HNMR (400 MFIz, CDC13) 7.76 (d, J 8.3 Hz, 2H), 7.35-7.29 (m, 2H), 5.62 (t, J 6.1 Hz, 1H), 3.70 (t, J= 5.8 Hz, 2H), 3.07 (q, J= 6.3 Hz, 2H),2.74 (s, 1H), 2.43 (s, 3H), 1.71 (ap p, J= 6.0 Hz, 2H). ‘HNMR data for this product corresponds with literature values.
91% With triethylamine In chloroform at 0 - 20℃; for 19h;
90% With triethylamine In dichloromethane at 0℃; for 5h;
90% With triethylamine at 20℃;
88% With triethylamine In dichloromethane
84% With anhydrous sodium carbonate In water monomer for 6.5h;
80% With triethylamine In dichloromethane at 0 - 20℃;
80% With triethylamine In dichloromethane at 0 - 20℃;
79% With triethylamine In dichloromethane at 0℃; for 0.25h;
78%
68% With triethylamine In dichloromethane at 0 - 25℃; for 1h;
68% With triethylamine In dichloromethane at 0℃; for 0.5h;
68% With triethylamine In dichloromethane at 0℃; for 0.5h;
With potassium carbonate In N,N-dimethyl-formamide at 125℃;
With triethylamine In tetrahydrofuran; water monomer at 0 - 20℃;
With triethylamine In dichloromethane at 20℃; for 16h;
With triethylamine In dichloromethane at 5℃; for 24h;
With triethylamine In dichloromethane at 0 - 20℃; for 13h;
With triethylamine In chloroform at 0 - 20℃;
In ethyl acetate at 20℃; for 2h; Typical procedure for the synthesis of starting materials General procedure: Tosylation: To a solution of p-toluenesulfonyl chloride (5 mmol, 1.0 equiv) in EtOAc (10 mL) was added proper alkanolamine (10 mmol, 2.0 equiv). The reaction mixture was stirred for 2 hours at room temperature. After completion of the reaction, the mixture was filtered through silica and washed with EtOAc. The residue was concentrated to give products, which were used to next step without further purification.
With triethylamine at 0 - 20℃; for 24h;
With triethylamine In dichloromethane at 0 - 20℃; for 10h;
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
With pyridine In dichloromethane at 0 - 20℃; for 1h;

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[2]Ohno, Hiroaki; Miyamura, Kumiko; Tanaka, Tetsuaki; Oishi, Shinya; Toda, Ayako; Takemoto, Yoshiji; Fujii, Nobutaka; Ibuka, Toshiro [Journal of Organic Chemistry, 2002, vol. 67, # 4, p. 1359 - 1367]
[3]Younai, Ashkaan; Zeng, Bi-Shun; Meltzer, Herbert Y.; Scheidt, Karl A. [Angewandte Chemie - International Edition, 2015, vol. 54, # 23, p. 6900 - 6904][Angew. Chem., 2015, vol. 54-127, # 23, p. 7004 - 7008]
[4]Current Patent Assignee: NORTHWESTERN UNIVERSITY (ILLINOIS) - WO2016/179184, 2016, A2 Location in patent: Paragraph 00029; 00030
[5]Kokotos, Christoforos G.; Aggarwal, Varinder K. [Chemical Communications, 2006, # 20, p. 2156 - 2158]
[6]Poloukhtine, Andrei; Popik, Vladimir V. [Journal of the American Chemical Society, 2007, vol. 129, # 40, p. 12062 - 12063]
[7]Comito, Robert J.; Finelli, Fernanda G.; Macmillan, David W. C. [Journal of the American Chemical Society, 2013, vol. 135, # 25, p. 9358 - 9361]
[8]Greenaway, Rebecca L.; Campbell, Craig D.; Chapman, Helen A.; Anderson, Edward A. [Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3187 - 3194]
[9]Angle, Steven R.; Belanger, Dominique S. [Journal of Organic Chemistry, 2004, vol. 69, # 13, p. 4361 - 4368]
[10]Elliott, Luke D.; Wrigglesworth, Joe W.; Cox, Brian; Lloyd-Jones, Guy C.; Booker-Milburn, Kevin I. [Organic Letters, 2011, vol. 13, # 4, p. 728 - 731]
[11]He, Tian; Gao, Wen-Chao; Wang, Wei-Kun; Zhang, Chi [Advanced Synthesis and Catalysis, 2014, vol. 356, # 5, p. 1113 - 1118]
[12]Bailey, Thomas R.; Garigipati, Ravi S.; Morton, Judith A.; Weinreb, Steven M. [Journal of the American Chemical Society, 1984, vol. 106, # 11, p. 3240 - 3245]
[13]Schirrmacher, Ralf; Mathiasch, Bernd; Schirrmacher, Esther; Radnic, Dragana; Roesch, Frank [Journal of labelled compounds and radiopharmaceuticals, 2003, vol. 46, # 10, p. 959 - 977]
[14]Walker, Stephen M.; Williams, Jodi T.; Russell, Alexander G.; Snaith, John S. [Tetrahedron Letters, 2005, vol. 46, # 39, p. 6611 - 6615]
[15]Williams, Jodi T.; Bahia, Perdip S.; Kariuki, Benson M.; Spencer, Neil; Philp, Douglas; Snaith, John S. [Journal of Organic Chemistry, 2006, vol. 71, # 6, p. 2460 - 2471]
[16]Williams, Jodi T.; Bahia, Perdip Singh; Snaith, John S. [Organic Letters, 2002, vol. 4, # 21, p. 3727 - 3730]
[17]Lee; Hashimoto; Ohta; Shudo; Okamoto [Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 8, p. 3046 - 3049]
[18]Augstein,J. et al. [Journal of Medicinal Chemistry, 1965, vol. 8, p. 356 - 367] Drandarov, Konstantin; Guggisberg, Armin; Hesse, Manfred [Helvetica Chimica Acta, 2002, vol. 85, # 4, p. 979 - 989]
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[22]Babu, Beneesh P.; Endo, Yoshinori; Baeckvall, Jan-E. [Chemistry - A European Journal, 2012, vol. 18, # 37, p. 11524 - 11527,4]
[23]Campbell, Craig D.; Greenaway, Rebecca L.; Holton, Oliver T.; Walker, P. Ross; Chapman, Helen A.; Russell, C. Adam; Carr, Greg; Thomson, Amber L.; Anderson, Edward A. [Chemistry - A European Journal, 2015, vol. 21, # 36, p. 12627 - 12639]
[24]Hwang, Joon Young; Shin, Jung Ha; Seong, Eun Young; Kang, Eun Joo [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 695 - 698]
[25]Chen, Anrong; Yu, Houjian; Yan, Jiaqi; Huang, Hanmin [Organic Letters, 2020, vol. 22, # 2, p. 755 - 759]
[26]Chen, Yang-Bo; Sun, Zhou; Wang, Ze-Shu; Ye, Long-Wu; Zhang, Hao-Wen; Zhu, Chunyin [Journal of the American Chemical Society, 2020, vol. 142, # 7, p. 3636 - 3644]
[27]Lorton, Charlotte; Saleh, Nidal; Voituriez, Arnaud [European Journal of Organic Chemistry, 2021, vol. 2021, # 22, p. 3340 - 3344]
[28]Hashimoto, Hisashi; Kawabata, Takeo; Takasu, Kiyosei; Ueda, Yoshihiro [Angewandte Chemie - International Edition, 2022, vol. 61, # 18][Angew. Chem., 2022, vol. 61, # 18]
  • 3
  • [ 110-87-2 ]
  • [ 13379-98-1 ]
  • [ 109774-82-5 ]
YieldReaction ConditionsOperation in experiment
95% With toluene-4-sulfonic acid In diethyl ether for 3h;
Yield given;
  • 4
  • [ 358-23-6 ]
  • [ 13379-98-1 ]
  • [ 264218-69-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 0℃; for 0.333333h;
  • 5
  • [ 13379-98-1 ]
  • [ 718633-51-3 ]
YieldReaction ConditionsOperation in experiment
79% With sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide In dichloromethane; water at 35℃; Inert atmosphere;
79% With sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide In dichloromethane; water at 35℃; for 18h; Inert atmosphere; 2 4-Methyl-N-(3-oxopropyl)benzenesulfonamide (II) [00031] To a mixture of N-(3 -hydroxypropyl)-4-methylbenzenesulfonamide (1.15 g, 5.00 mmol), TEMPO (0.078 g, 0.50 mmol, 0.10 equiv), NaTO4 (1.77 g, 8.25 mmol, 1.65 equiv) and NaBr (0.085 g, 0.825 mmol, 0.165 equiv) was added CH2C12/H20 (45:55, 20.0 mL, 0.25 M). The resulting biphasic mixture was heated to 35 °C. Upon completion of the reaction (18 h; monitored by TLC), the organic layer was separated, and the aqueous layer was extracted with CH2C12. The combined organic layers were concentrated in vacuo, and the residue was partitioned between EtOAc and sat. aq. Na2 S203. The organic layer was then washed successively with H20 and brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification by column chromatography (40:60 to 50:50 EtOAc/hexanes) provided 4-methyl-N- (3-oxopropyl)benzenesulfonamide (0.903 g, 3.97 mmol, 79% yield) as a yellow oil.[00032] Analytical data for II: ‘HNMR (500 IVIFIz, CDC13) 9.73 (s, 1H), 7.74 (d, J 8.3 Hz, 2H), 7.32 (d, J= 8.0 Hz, 2H), 4.92 (t, J= 6.6 Hz, 1H), 3.21 (q, J 6.1 Hz, 2H), 2.75 (t, J = 5.8 Hz, 2H), 2.43 (s, 3H). ‘H NMR data for this product corresponds with literature values.
78% With Dess-Martin periodane In dichloromethane for 5h;
66% With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;
65% With oxalyl dichloride; dimethyl sulfoxide; diisopropylamine In dichloromethane at -78 - 0℃; for 1.33333h;
With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 1.33333h;
With pyridinium chlorochromate In dichloromethane at 0℃; for 2h; Molecular sieve;
2.15 g With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere;

  • 6
  • [ 13379-98-1 ]
  • [ 124-63-0 ]
  • [ 444119-31-7 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In chloroform at 0℃; for 0.5h;
  • 7
  • [ 21378-06-3 ]
  • [ 13379-98-1 ]
  • [ 686273-50-7 ]
YieldReaction ConditionsOperation in experiment
62% With caesium carbonate In N,N-dimethyl-formamide for 1.5h;
With caesium carbonate In N,N-dimethyl-formamide at 25℃;
  • 8
  • [ 931-42-0 ]
  • [ 13379-98-1 ]
  • [ 686273-51-8 ]
YieldReaction ConditionsOperation in experiment
65% With caesium carbonate In N,N-dimethyl-formamide for 1.5h;
With caesium carbonate In N,N-dimethyl-formamide at 25℃;
  • 9
  • [ 932-86-5 ]
  • [ 13379-98-1 ]
  • [ 686273-52-9 ]
YieldReaction ConditionsOperation in experiment
60% With caesium carbonate In N,N-dimethyl-formamide for 1.5h;
With caesium carbonate In N,N-dimethyl-formamide at 25℃;
  • 10
  • [ 13379-98-1 ]
  • [ 90149-86-3 ]
  • [ 686273-56-3 ]
YieldReaction ConditionsOperation in experiment
59% With caesium carbonate In N,N-dimethyl-formamide for 1.5h;
With caesium carbonate In N,N-dimethyl-formamide at 25℃;
  • 11
  • [ 13379-98-1 ]
  • [ 870-63-3 ]
  • [ 475292-74-1 ]
YieldReaction ConditionsOperation in experiment
93% With caesium carbonate In acetonitrile at 25℃; for 18h;
86% With caesium carbonate In N,N-dimethyl-formamide for 1.5h;
86% With caesium carbonate In N,N-dimethyl-formamide at 25℃; for 1.5h;
55% Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil for 1h; Stage #2: prenyl bromide In N,N-dimethyl-formamide; mineral oil for 18h;
Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: prenyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 8h;

  • 12
  • [ 676-97-1 ]
  • [ 13379-98-1 ]
  • [ 892860-54-7 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In tetrahydrofuran Heating; Stage #2: methylphosphonic acid dichloroanhydride In tetrahydrofuran Heating;
  • 13
  • [ 824-72-6 ]
  • [ 13379-98-1 ]
  • 2-phenyl-3-(toluene-4-sulfonyl)-[1,3,2]oxazaphosphinane 2-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In tetrahydrofuran Heating; Stage #2: P,P-dichlorophenylphosphine oxide In tetrahydrofuran Heating;
  • 14
  • [ 7206-98-6 ]
  • [ 13379-98-1 ]
  • [ 882053-93-2 ]
YieldReaction ConditionsOperation in experiment
66% With caesium carbonate In N,N-dimethyl-formamide for 1.5h;
  • 15
  • [ 13379-98-1 ]
  • [ 90149-87-4 ]
  • [ 882053-94-3 ]
YieldReaction ConditionsOperation in experiment
63% With caesium carbonate In N,N-dimethyl-formamide for 1.5h;
  • 16
  • [ 13379-98-1 ]
  • [ 770-12-7 ]
  • 2-phenoxy-3-(toluene-4-sulfonyl)-[1,3,2]oxazaphosphinane 2-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In tetrahydrofuran Heating; Stage #2: O-phenyl phosphorodichloridate In tetrahydrofuran Heating;
  • 17
  • [ 13379-98-1 ]
  • [ 3355-28-0 ]
  • [ 882053-90-9 ]
YieldReaction ConditionsOperation in experiment
63% With caesium carbonate In N,N-dimethyl-formamide for 40h;
  • 18
  • [ 13379-98-1 ]
  • [ 676-98-2 ]
  • [ 892860-50-3 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In tetrahydrofuran for 1h; Heating; Stage #2: methylphosphonothioic dichloride In tetrahydrofuran for 3h; Heating;
  • 19
  • [ 13379-98-1 ]
  • [ 3497-00-5 ]
  • [ 892860-52-5 ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In tetrahydrofuran Heating; Stage #2: phenylthiophosphonic acid dichloride In tetrahydrofuran Heating;
  • 20
  • [ 13379-98-1 ]
  • [ 18162-48-6 ]
  • [ 115306-77-9 ]
YieldReaction ConditionsOperation in experiment
93% With 1H-imidazole; dmap In dichloromethane at 0℃; for 2.5h;
78% With 1H-imidazole; dmap In dichloromethane at 0℃; Inert atmosphere;
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h;
With 1H-imidazole In dichloromethane at 20℃; for 22h;

  • 21
  • [ 13379-98-1 ]
  • [ 882054-04-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 63 percent / cesium carbonate / dimethylformamide / 40 h 2: hydrogen; quinoline / palladium on barium sulfate / methanol / 2 h
  • 22
  • [ 13379-98-1 ]
  • [ 475292-56-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 86 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 67 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C
Multi-step reaction with 2 steps 1: 93 percent / Cs2CO3 / acetonitrile / 18 h / 25 °C 2: 67 percent / PCC; Celite / CH2Cl2 / 2 h / 25 °C
Multi-step reaction with 2 steps 1: 86 percent / Cs2CO3 / dimethylformamide / 1.5 h / 25 °C 2: 67 percent / PCC; celite / CH2Cl2 / 2 h / 25 °C
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h 1.2: 18 h 2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C

  • 23
  • [ 13379-98-1 ]
  • [ 475292-57-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 62 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 77 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C
  • 24
  • [ 13379-98-1 ]
  • [ 475292-58-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 65 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 85 percent / pyridinium chlorochromate; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / molecular sieves 4 Angstroem / CH2Cl2 / 1.25 h
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: 83 percent / TPAP; NMO; 4 Angstroem molecular sieves / 25 °C
  • 25
  • [ 13379-98-1 ]
  • [ 475292-59-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 60 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 67 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C
  • 26
  • [ 13379-98-1 ]
  • (3RS,4SR)-3-[(E)-1-ethylprop-1-enyl]-1-(toluene-4-sulfonyl)piperidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 62 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 77 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: hydrochloric acid / CH2Cl2 / 16 h / -78 °C
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: HCl / CH2Cl2; H2O / 16 h / -78 °C
  • 27
  • [ 13379-98-1 ]
  • (3RS,4RS)-3-(cyclopent-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 65 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 85 percent / pyridinium chlorochromate; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / molecular sieves 4 Angstroem / CH2Cl2 / 1.25 h 3: 53 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: 83 percent / TPAP; NMO; 4 Angstroem molecular sieves / 25 °C 3: 53 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C
  • 28
  • [ 13379-98-1 ]
  • (3RS,4SR)-3-(cyclopent-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 65 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 85 percent / pyridinium chlorochromate; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / molecular sieves 4 Angstroem / CH2Cl2 / 1.25 h 3: 22 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: 83 percent / TPAP; NMO; 4 Angstroem molecular sieves / 25 °C 3: 22 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C
  • 29
  • [ 13379-98-1 ]
  • [ 475292-60-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 59 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 61 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C
  • 30
  • [ 13379-98-1 ]
  • (3RS,4RS)-3-(cyclohex-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 60 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 67 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: 74 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: 74 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C
  • 31
  • [ 13379-98-1 ]
  • (3RS,4SR)-3-(cyclohex-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 60 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 67 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: 4 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: 4 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C
  • 32
  • [ 13379-98-1 ]
  • (3RS,4RS)-3-(cyclohept-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 59 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 61 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: 61 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: 61 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C
  • 33
  • [ 13379-98-1 ]
  • (3RS,4SR)-3-(cyclohept-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 59 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 61 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: 20 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: 20 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C
  • 34
  • [ 13379-98-1 ]
  • [ 882054-05-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 63 percent / cesium carbonate / dimethylformamide / 40 h 2: hydrogen; quinoline / palladium on barium sulfate / methanol / 2 h
  • 35
  • [ 13379-98-1 ]
  • (3RS,4SR)-3-[(Z)-1-ethylprop-1-enyl]-1-(toluene-4-sulfonyl)piperidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 62 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 77 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: hydrochloric acid / CH2Cl2 / 16 h / -78 °C
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: HCl / CH2Cl2; H2O / 16 h / -78 °C
  • 36
  • [ 13379-98-1 ]
  • [ 321835-85-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 82 percent / Et3N / acetonitrile / 4 h / Heating 3: 90 percent / Cu(Ac)2 / 24 h / 20 °C 4: 90 percent / Et3N / CHCl3 / 0.5 h / 0 °C
  • 37
  • [ 13379-98-1 ]
  • [ 444119-35-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 82 percent / Et3N / acetonitrile / 4 h / Heating 3: 90 percent / Cu(Ac)2 / 24 h / 20 °C
  • 38
  • [ 13379-98-1 ]
  • [ 373360-25-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 82 percent / Et3N / acetonitrile / 4 h / Heating 3: 90 percent / Cu(Ac)2 / 24 h / 20 °C 4: 90 percent / Et3N / CHCl3 / 0.5 h / 0 °C 5: 83 percent / Cs2CO3 / dimethylformamide
  • 39
  • [ 13379-98-1 ]
  • [ 444119-34-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 79 percent / Et3N / acetonitrile / 4 h / Heating 3: 87 percent / Cu(Ac)2 / 24 h / 20 °C
  • 40
  • [ 13379-98-1 ]
  • [ 444119-36-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 79 percent / Et3N / acetonitrile / 4 h / Heating 3: 87 percent / Cu(Ac)2 / 24 h / 20 °C 4: 92 percent / Et3N / CHCl3 / 0.5 h / 0 °C
  • 41
  • [ 13379-98-1 ]
  • [ 444119-37-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 79 percent / Et3N / acetonitrile / 4 h / Heating 3: 87 percent / Cu(Ac)2 / 24 h / 20 °C 4: 92 percent / Et3N / CHCl3 / 0.5 h / 0 °C 5: 75 percent / Cs2CO3 / dimethylformamide
  • 42
  • [ 13379-98-1 ]
  • [ 89578-72-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / p-TsOH*H2O / diethyl ether / 3 h 2: 1.) KH; 2.) HCl / 1.) DMF-mineral oil, 2.5 h, 50 deg C; 2.) MeOH, 1.5 h, RT
  • 43
  • [ 13379-98-1 ]
  • [ 89578-75-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 100 percent / aq. LiOH / methanol / 15 h / Ambient temperature
  • 44
  • [ 13379-98-1 ]
  • [ 89578-74-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature
  • 45
  • [ 13379-98-1 ]
  • [ 89578-73-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / p-TsOH*H2O / diethyl ether / 3 h 2: 1.) KH; 2.) HCl / 1.) DMF-mineral oil, 2.5 h, 50 deg C; 2.) MeOH, 1.5 h, RT 3: 95 percent / pyridine / CH2Cl2 / 0.25 h / 0 °C
  • 46
  • [ 13379-98-1 ]
  • [ 89578-78-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 100 percent / aq. LiOH / methanol / 15 h / Ambient temperature 4: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 45 h 5: 82 percent / dimethylformamide / 18 h / -20 °C 6: 80 percent / Et3N / CH2Cl2 / 1 h / -15 - 5 °C 7: 58 percent / K2CO3 / acetonitrile / 24 h / Heating
  • 47
  • [ 13379-98-1 ]
  • [ 89578-76-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 100 percent / aq. LiOH / methanol / 15 h / Ambient temperature 4: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 45 h 5: 82 percent / dimethylformamide / 18 h / -20 °C
  • 48
  • [ 13379-98-1 ]
  • [ 89578-83-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 100 percent / aq. LiOH / methanol / 15 h / Ambient temperature 4: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 45 h
  • 49
  • [ 13379-98-1 ]
  • [ 89578-77-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 100 percent / aq. LiOH / methanol / 15 h / Ambient temperature 4: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 45 h 5: 82 percent / dimethylformamide / 18 h / -20 °C 6: 80 percent / Et3N / CH2Cl2 / 1 h / -15 - 5 °C
  • 50
  • [ 13379-98-1 ]
  • [ 89596-61-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 95 percent / p-TsOH*H2O / diethyl ether / 3 h 2: 1.) KH; 2.) HCl / 1.) DMF-mineral oil, 2.5 h, 50 deg C; 2.) MeOH, 1.5 h, RT 3: 95 percent / pyridine / CH2Cl2 / 0.25 h / 0 °C 4: 70 percent / diisopropylethylamine / CH2Cl2 / 13 h / Ambient temperature
  • 51
  • [ 13379-98-1 ]
  • [ 109774-74-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 2: 79 percent / K2CO3 / acetonitrile / 24 h / 80 °C 3: 90 percent / MeOH / pTsOH / 1 h / Ambient temperature 4: 98 percent / Et3N / CH2Cl2 / 2 h / -78 - 25 °C 5: 65 percent / Cs2CO3 / dimethylformamide / 7 h / 80 °C
  • 52
  • [ 13379-98-1 ]
  • [ 109774-73-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: 79 percent / K2CO3 / acetonitrile / 24 h / 80 °C 3: 90 percent / MeOH / pTsOH / 1 h / Ambient temperature
  • 53
  • [ 13379-98-1 ]
  • [ 109789-74-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 2: 79 percent / K2CO3 / acetonitrile / 24 h / 80 °C 3: 90 percent / MeOH / pTsOH / 1 h / Ambient temperature 4: 98 percent / Et3N / CH2Cl2 / 2 h / -78 - 25 °C
  • 54
  • [ 13379-98-1 ]
  • [ 3245-96-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. NaOH / Heating 2: PBr3 / benzene
  • 55
  • [ 13379-98-1 ]
  • [ 47473-89-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: HBr / acetic acid
  • 56
  • [ 13379-98-1 ]
  • [ 47528-43-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aq. NaOH / Heating 2: PBr3 / benzene
  • 57
  • [ 1125-88-8 ]
  • [ 13379-98-1 ]
  • [ 107273-07-4 ]
YieldReaction ConditionsOperation in experiment
With camphor-10-sulfonic acid In 1,2-dichloro-ethane at 20 - 70℃;
  • 58
  • [ 50-00-0 ]
  • [ 13379-98-1 ]
  • [ 7344-11-8 ]
YieldReaction ConditionsOperation in experiment
94% With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve;
  • 59
  • [ 13379-98-1 ]
  • [ 100-52-7 ]
  • [ 107273-07-4 ]
YieldReaction ConditionsOperation in experiment
91% With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve;
  • 60
  • [ 13379-98-1 ]
  • [ 75-07-0 ]
  • [ 1190398-19-6 ]
YieldReaction ConditionsOperation in experiment
82% With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve;
  • 61
  • [ 13379-98-1 ]
  • [ 123-38-6 ]
  • [ 1190398-20-9 ]
YieldReaction ConditionsOperation in experiment
100% With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve;
  • 62
  • [ 34414-28-3 ]
  • [ 13379-98-1 ]
  • [ 1254356-81-4 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With caesium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: (E)-1-chloro-4-acetoxybut-2-ene With tetra-(n-butyl)ammonium iodide In acetonitrile at 0 - 20℃; for 12h;
  • 63
  • [ 13379-98-1 ]
  • [ 607389-95-7 ]
  • [ 1254356-85-8 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With caesium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: (E)-1-acetoxy-4-chloro-2-[(triethyl)silyl]but-2-ene With tetra-(n-butyl)ammonium iodide In acetonitrile at 0 - 20℃; for 12h;
  • 64
  • [ 1663-39-4 ]
  • [ 13379-98-1 ]
  • [ 1265900-35-3 ]
YieldReaction ConditionsOperation in experiment
38% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 16h; Inert atmosphere;
  • 65
  • [ 141-32-2 ]
  • [ 13379-98-1 ]
  • [ 1265900-33-1 ]
YieldReaction ConditionsOperation in experiment
83% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 30℃; for 21h; Inert atmosphere;
  • 66
  • [ 13379-98-1 ]
  • [ 292638-85-8 ]
  • [ 1265900-37-5 ]
YieldReaction ConditionsOperation in experiment
71% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 6h; Inert atmosphere;
  • 67
  • [ 13379-98-1 ]
  • [ 79-10-7 ]
  • [ 1265900-39-7 ]
YieldReaction ConditionsOperation in experiment
32% With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 6h; Inert atmosphere;
  • 68
  • [ 13379-98-1 ]
  • [ 1296794-23-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1H-imidazole; dmap / dichloromethane / 0 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere
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