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Product Details of [ 63273-48-3 ]

CAS No. :	63273-48-3	MDL No. :	MFCD09923385
Formula :	C₁₃H₁₅NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	233.27	Pubchem ID :	-
Synonyms :

Safety of [ 63273-48-3 ]

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Application In Synthesis of [ 63273-48-3 ]

* 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.

Upstream synthesis route of [ 63273-48-3 ]
Downstream synthetic route of [ 63273-48-3 ]

[ 63273-48-3 ] Synthesis Path-Upstream 1~2

1
[ 63273-48-3 ]
[ 954-81-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-Bromosuccinimide; triphenylphosphine In dichloromethane for 3 h;	A solution of 5-phthalimido-1-pentanol (0.53 g, 2.3 mmol) andtriphenylphosphine (0.66 g, 2.5 mmol) in dichloromethane(25 mL) was cooled to 0 C. N-Bromosuccinimide (0.45 g,2.5 mmol) was added portion-wise over 10 min and stirring wascontinued at 0 C for 3 h. The reaction mixture diluted with dichloromethane(9 mL) and extracted with water (3 15 mL) and brine(15 mL). The organics were dried over sodium sulfate and concentratedunder reduced pressure. The residue was purified on silicagel (30percent ethyl acetate/hexane) to yield the product as a clear colorlessoil (0.54 g, 1.82 mmol, 80percent). 1H NMR (500 MHz, CDCl3) d 7.82(m, 2H), 7.71 (m, 2H), 3.68 (t, 2H, J = 7.5 Hz), 3.38 (t, 2H, J = 7 Hz),1.88 (m, 2H), 1.69 (m, 2H), 1.46 (m, 2H); 13C NMR (125 MHz,CDCl3) d 168.31, 133.86, 132.01, 123.13, 37.56, 33.34, 32.11,27.65, 25.31
45%	With phosphorus tribromide In diethyl ether	Then, 16.2 g of 5-phthalimido-1-pentanol was dissolved in 350 ml of diethyl ether, and 4.3 ml of phosphorus tribromide was added dropwise at 0° C. The reaction solution was stirred at room temperature for 9 hours and neutralized with saturated aqueous sodium hydrogen carbonate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo for removal of the solvent. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to give 9.2 g of 1-bromo-5-phthalimidopentane in a yield of 45percent. Mass(m/z): 296(M+) 216 160; ¹H-NMR(CDCl₃): 1.44-1.55(2H,m) 1.63-1.77(2H,m) 1.86-2.00(2H,m) 3.37-3.42(2H,m) 3.67-3.73(2H,m) 7.68-7.75(2H,m) 7.81-7.88(2H,m).

Reference： [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4602 - 4608
[2] Patent: US6255321, 2001, B1,
[3] Synthetic Communications, 1985, vol. 15, # 14, p. 1277 - 1290
[4] Journal of Medicinal Chemistry, 2001, vol. 44, # 19, p. 3175 - 3186

2
[ 85-44-9 ]
[ 2508-29-4 ]
[ 7789-60-8 ]
[ 63273-48-3 ]
[ 954-81-4 ]

Reference： [1] Patent: US4705892, 1987, A,

[ 63273-48-3 ] Synthesis Path-Downstream 1~11

1
[ 85-44-9 ]
[ 2508-29-4 ]
[ 63273-48-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 145℃; for 0.5h;
100%	In ethanol Heating / reflux;	1 1 ,8-naphthalic anhydride (2.8 g, 19 mmol) was added to a solution 6-Amino- pentan-1 -ol (2 g, 19 mmol) in absolute ethanol (140 ml_). The reaction mixture was heated at reflux overnight. Removal of the solvent and purification by chromatography on alumina (CH2CI2/MeOH, 50:1 ) yielded 2-(6-hydroxy- pentyl)-isoindole-1 ,3-dione (Hamilton, R., "A convenient synthesis of N- protected diphenyl phosphonate ester analogues of ornithine, lysine and homolysine", Tetrahedron Letters, 1993, 34(17), 2847-50) (4.5 g, 100%) as a foam. 1H-NMR [CDCI3, δ, ppm]: 8.62 (m, 2H), 8.22 (m, 2H), 3.69 (m, 2H, CH2O), 3.58 (m, 2H, CH2NO), 1.72 (m, 2H, CH2), 1.41 (m, 4H, CH2).
100%	at 145℃; for 0.5h;

100%	for 0.5h; Inert atmosphere; Heating;
99%	In toluene Heating;
99%	With triethylamine In toluene at 125℃; for 3h; Inert atmosphere; Dean-Stark;
99%	at 145℃; for 0.5h; Inert atmosphere;
95%	at 145℃; for 16h; Inert atmosphere;
94%	at 130℃; for 16h;
93%	In toluene for 24h; Reflux; Dean-Stark; Inert atmosphere;	2-(5-Hydroxypentyl)isoindoline-1,3-dione 5-Amino-1-pentanol (18.7 g, 181 mmol) and phthalic anhydride (26.8 g, 181 mmol) were heated to reflux in 181 mL toluene with a Dean-Stark condenser attached for 24 hours. The mixture was cooled to room temperature, transferred to a separatory funnel using ethyl acetate, washed once with brine, dried with sodium sulfate, and concentrated under vacuum to provide 39.2 g (93%) 2-(5-hydroxypentyl)isoindoline-1,3-dione as a white solid.
90%	In toluene for 3h; Heating;
89%	In toluene for 24h; Reflux; Inert atmosphere;
83%	With magnesium sulfate In toluene Heating;
74%	In toluene	7 Preparation of 5-(4-chlorophenylsulfonyl)pentanamine Example 7 Preparation of 5-(4-chlorophenylsulfonyl)pentanamine 10 g (96.9 mmo)of 5-amino-l-pentanol was dissolved in 300 ml of toluene and refluxed together with 17.2 g (116 mmol) of phthalic anhydride at 120° C. for 24 hours. The solvent was distilled off in vacuo, and the residue was purified by silica gel column chromatography (eluent; chloroform) to give 16.6 g of 5-phthalimido-1-pentanol in a yield of 74%. Mass(m/z): 233(M+) 203 160; 1H-NMR(CDCl3): 1.37-1.48(2H,m) 1.58-1.78(4H,m) 3.62-3.73(4H,m) 7.68-7.74(2H,m) 7.81-7.87(2H,m).
72%	In toluene for 3h; Reflux;
48%	With triethylamine In toluene at 130℃; for 3h;
	In toluene for 3h; Heating;
	In toluene Yield given;
	With triethylamine In toluene Heating;
	With triethylamine In toluene at 125℃; for 3h;
19.77 g (84.0 mmol, 84%)	In toluene	56.A A. A. 5-Phthalimidopentanol: A mixture of 10.317 g (100 mmol) 5-amino-1-pentanol and 14.812 g (100 mmol) phthalic anhydride in 200 mL toluene was stirred 18 h under nitrogen at reflux while employing a Dean-Stark trap for removal of water. The reaction was allowed to cool to room temperature and solvent was removed. The residue was flash column chromatographed (1;1 hexanes-ethyl acetate) to provide 19.77 g (84.0 mmol, 84%) of a clear liquid; NMR(CDCl3): 7.66-7.88 (m, 4H), 3.59-3.75 (m, 4H), 1.32-1.79 (m, 6H); Mass spectrum: m/z 234 (M+H).
	In toluene at 100℃; for 4h;	A mixture of 5-amino-1-pentanol (ALDRICH, 0.333 mL, 3.2mmol), phthalic anhydride (PROBUS, 533mg, 3.6mmol) in dry toluene (Panreac, 10 mL) was heated at 100°C for 4hours. The reaction mixture was diluted with 70mL of dichloromethane, washed twice with 50ml_ of hydrochloric acid 1N and with 50mL of aqueous sodium bicarbonate saturated solution, dried over sodium sulfate and evaporated to dryness. The residue was purified by flash cromatography using dichloromethane/methanol 20:1 as eluant to give 2-(5-hydroxypentyl)-1H-isoindole-1,3(2H)-dione which was dissolved in 30mL of dichloromethane (PANREAC) and treated with triethylamine (SIGMA, 0.443 ml_, 3.18mmol) and methanesulfonyl chloride (ALDRICH, 0,217 mL, 2.8mmol). The reaction mixture was stirred overnight at room temperature, then, diluted with 50ml_ of dichloromethane, washed with 50ml_ of hydrochloric acid 1N, 50ml_ of aqueous sodium bicarbonate saturated solution and 50ml_ of brine, dried over sodium sulfate and evaporated to dryness to give Intermediate 39. [ES+ MS] m/z: 312 (MH)+.
		Synthesis of 5-phthalimido-1-pentanol (8) Synthesis of 5-phthalimido-1-pentanol (8) 5-Amino-1-pentanol (1.00 g, 9.7 mmol) was mixed with phthalic anhydride (1.44 g, 9.7 mmol) and irradiated for 5 min at 150° C. in a microwave oven. The reaction mixture was dried in vacuo to afford the product 5-phthalimido-1-pentanol (8) as a yellow viscous oil (2.26 g, 100%). 1H NMR (300 MHz, CDCl3): δ 1.36-1.47 (m, 2H, H3), 1.58-1.80 (m, 4H, H2 and H4), 3.63 (t, J=6.5 Hz, 2H, H1), 3.69 (t, J=7.2 Hz, 2H, H5), 7.69-7.73 (m, 2H, Pht), 7.82-7.85 (m, 2H, Pht). 13C NMR (50 MHz, CDCl3): δ 18.50 (C3), 24.18 (C4), 34.27 (C2), 31.89 (C5), 56.18 (C1), 117.14, 125.99, 127.96 (Pht), 165.32 (CO). HR-MS (ESI+) Found: m/z 234.1129; C13H16NO3 (M+H)+ requires 234.1130 and found m/z 256.0950; C13H15NO3Na (M+Na)+ requires 256.0950.
	at 145℃; Inert atmosphere;
	In benzene Dean-Stark;
	at 140℃;	88 Phtalic anhydride (7.6 g, 51.3 mmol) and 5-amino-pentan-l-ol (5.0 ml, 53.9 mmol) were heated to 140 0C overnight, cooled to rt, extracted with EtOAc/NaHCO3 (aq., sat.). The organic phase was subsequently washed with water, 10% citric acid, brine, dried (MgSO4) and concentrated to yield compound 88. 1H-NMR (CDCI3): δ 7.83 (m, 2H), 7.70 (m, 2H), 3.69 (t, 2H), 3.63 (t, 2H), 1.71 (m, 2H), 1.60 (m, 3H), 1.41 (m, 2H).
500 mg	at 140℃; for 0.5h;

Reference： [1]Jackson, Delwin S.; Fraser, Stephanie A.; Ni, Li-Ming; Kam, Chih-Min; Winkler, Ulrike; Johnson, David A.; Froelich, Christopher J.; Hudig, Dorothy; Powers, James C. [Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2289 - 2301]
[2]Current Patent Assignee: ORYZON GENOMICS S.A. - WO2009/7399, 2009, A1 Location in patent: Page/Page column 31
[3]Location in patent: experimental part Wang, Xin; Mealer, David; Rodgers, Lacey; Sandoval, Karin; Witt, Ken; Stidsen, Carsten; Ankersen, Michael; Crider, A. Michael [Letters in drug design and discovery, 2012, vol. 9, # 7, p. 655 - 662]
[4]Gorecki, Lukas; Uliassi, Elisa; Bartolini, Manuela; Janockova, Jana; Hrabinova, Martina; Hepnarova, Vendula; Prchal, Lukas; Muckova, Lubica; Pejchal, Jaroslav; Karasova, Jana Z.; Mezeiova, Eva; Benkova, Marketa; Kobrlova, Tereza; Soukup, Ondrej; Petralla, Sabrina; Monti, Barbara; Korabecny, Jan; Bolognesi, Maria Laura [ACS Chemical Neuroscience, 2021, vol. 12, # 9, p. 1698 - 1715]
[5]Miller, David J.; Hammond, Stephen M.; Anderluzzi, Daniela; Bugg, Timothy D. H. [Journal of the Chemical Society. Perkin transactions I, 1998, # 1, p. 131 - 142]
[6]Storz, Michael P.; Allegretta, Giuseppe; Kirsch, Benjamin; Empting, Martin; Hartmann, Rolf W. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 32, p. 6094 - 6104]
[7]Zhang, Wen; Carpenter, Keith L.; Lin, Song [Angewandte Chemie - International Edition, 2020, vol. 59, # 1, p. 409 - 417][Angew. Chem., 2020, vol. 132, # 59, p. 417 - 425,9]
[8]Allegretti, Paul A.; Ferreira, Eric M. [Journal of the American Chemical Society, 2013, vol. 135, # 46, p. 17266 - 17269]
[9]Sall, Daniel J.; Arfsten, Ann E.; Bastian, Jolie A.; Denney, Michael L.; Harms, Cathy S.; McCowan, Jefferson R.; Morin Jr., John M.; Rose, Jack W.; Scarborough, Robert M.; Smyth, Mark S.; Um, Suzane L.; Utterback, Barbara G.; Vasileff, Robert T.; Wikel, James H.; Wyss, Virginia L.; Jakubowski, Joseph A. [Journal of Medicinal Chemistry, 1997, vol. 40, # 18, p. 2843 - 2857]
[10]Russo, Christopher M.; Adhikari, Arijit A.; Wallach, Daniel R.; Fernandes, Sandra; Balch, Amanda N.; Kerr, William G.; Chisholm, John D. [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5344 - 5348]
[11]Xiao, Xiangshu; Antony, Smitha; Kohlhagen, Glenda; Pommier, Yves; Cushman, Mark [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 19, p. 5147 - 5160]
[12]Jeon, Jinwon; Ryu, Ho; Lee, Changseok; Cho, Dasol; Baik, Mu-Hyun; Hong, Sungwoo [Journal of the American Chemical Society, 2019] Jeon, Jinwon; Ryu, Ho; Lee, Changseok; Cho, Dasol; Baik, Mu-Hyun; Hong, Sungwoo [Journal of the American Chemical Society, 2019, vol. 141, # 25, p. 10048 - 10059]
[13]Ninomiya; Satoh; Sugiyama; Shinomiya; Kuroda [Chemical Communications, 1996, # 15, p. 1825 - 1826]
[14]Current Patent Assignee: KAKEN PHARMACEUTICAL CO LTD - US6255321, 2001, B1
[15]Rubinshtein, Mark; James, Carrie R.; Young, Jennifer L.; Ma, Yanyan J.; Kobayashi, Yoshihisa; Gianneschi, Nathan C.; Yang, Jerry [Organic Letters, 2010, vol. 12, # 15, p. 3560 - 3563]
[16]Location in patent: experimental part Pascale, Rossana; Carocci, Alessia; Catalano, Alessia; Lentini, Giovanni; Spagnoletta, Anna; Cavalluzzi, Maria Maddalena; De Santis, Francesco; De Palma, Annalisa; Scalera, Vito; Franchini, Carlo [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 16, p. 5903 - 5914]
[17]Payne, Linda S.; Boger, Joshua [Synthetic Communications, 1985, vol. 15, # 14, p. 1277 - 1290]
[18]Hamilton; Walker; Walker [Tetrahedron Letters, 1993, vol. 34, # 17, p. 2847 - 2850]
[19]Wang, Chia-Lin J.; Taylor, Thelma L.; Mical, Alfred J.; Spitz, Susan; Reilly, Thomas M. [Tetrahedron Letters, 1992, vol. 33, # 50, p. 7667 - 7670]
[20]Joossens; Van Der Veken; Lambeir; Augustyns; Haemers [Journal of Medicinal Chemistry, 2004, vol. 47, # 10, p. 2411 - 2413]
[21]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US5710159, 1998, A
[22]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2006/27211, 2006, A1 Location in patent: Page/Page column 64-65
[23]Current Patent Assignee: MONASH UNIVERSITY - US2012/225962, 2012, A1
[24]Kannan Sivaraman, Komagal; Paiardini, Alessandro; Sieńczyk, Marcin; Ruggeri, Chiara; Oellig, Christine A.; Dalton, John P.; Scammells, Peter J.; Drag, Marcin; McGowan, Sheena [Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5213 - 5217]
[25]Rezazadeh, Sina; Devannah, Vijayarajan; Watson, Donald A. [Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8110 - 8113]
[26]Current Patent Assignee: ONXEO - WO2010/142735, 2010, A1 Location in patent: Page/Page column 64
[27]Kokkala, Paraskevi; Rajeshkumar, Thayalan; Mpakali, Anastasia; Stratikos, Efstratios; Vogiatzis, Konstantinos D.; Georgiadis, Dimitris [Organic Letters, 2021, vol. 23, # 5, p. 1726 - 1730]

2
[ 2508-29-4 ]
[ 22509-74-6 ]
[ 63273-48-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	In benzene for 5h; Ambient temperature;
84%	In benzene	11 Preparation of Other Compounds AF. 5-phthalimido-1-pentanol (III-33). A solution of 5-amino-1-pentanol (5.00 g, 48.5 mmol) in benzene (150 ml) was treated with N-carboethoxyphthalimide (11.0 g, 50.2 mmol) and stirred at room temperature for 5 h. Concentration in vacuo and flash chromatography (25% ethyl acetate/petroleum ether) yielded III-33 (9.6 mg, 84% yield) as a clear, colorless oil: UV (9.65*10-4 M, acetonitrile) λmax 292.0 (ε212), 242.4 (226) nm; IR (CHCl3) 3460 (br), 2940 (s), 2860 (s), 1770 (s), 1710 (s), 1610 (s), 1470 (s), 1440 (s), 1400 (s), 1370 (s), 1190 (m), 1170 (m), 1130 (m), 1050 (s), 960 (m), 890 (m), 875 (m), 790 (m), 720 (s) cm-1; 1 H NMR (500 MHz, CDCl3) δ7.72-7.70 (m, 2H), 3.69 (t, J=7.2 Hz, 1H), 3.64 (t, J=6.5 Hz, 1H), 2.17 (br s, 1H), 1.74-1.59 (m, 2H), 1.46-1.40 (m, 1H); 13 C NMR (125 MHz, CDCl3) δ169.39, 133.78, 131.96, 123.05, 62.34, 37.74, 32.03, 28.22, 22.93; high resolution mass spectrum (Cl, NH3) m/z 234.1108 [(M+H)+; calcd for C13 H15 NO3: 234.1129].
84%	In ethyl acetate; Petroleum ether; benzene	7.K K. K. 5-Phthalimido-1-pentanol To a solution of 5-amino-1-pentanol (5.00 g, 48.5 mmol) in benzene (150 mL) was added N-carboethoxyphthalimide (11.0 g, 50.2 mmol) and the solution was stirred at room temperature for 5 h). The solvents were removed under reduced pressure to yield a yellow oil. Purification by flash column chromatography using 25% ethyl acetate in petroleum ether yielded the target compound as a clear colorless oil (9.6 mg, 84%).

84%	In benzene	11 AF. 5-Phthalimido-1-pentanol (III-33) AF. 5-Phthalimido-1-pentanol (III-33) A solution of 5-amino-1-pentanol (5.00 g, 48.5 mmol) in benzene (150 ml) was treated with N-carboethoxyphthalimide (11.0 g, 50.2 mmol) and stirred at room temperature for 5 h. Concentration in vacuo and flash chromatography (25% ethyl acetate/petroleum ether) yielded III-33 (9.6 mg, 84% yield) as a clear, colorless oil: UV (9.65*10-4 M, acetonitrile) λmax 292.0 (ε212), 242.4 (226) nm; IR (CHCl3) 3460 (br), 2940 (s), 2860 (s), 1770 (s), 1710 (s), 1610 (s), 1470 (s), 1440 (s), 1400 (s), 1370 (s), 1190 (m), 1170 (m), 1130 (m), 1050 (s), 960 (m), 890 (m), 875 (m), 790 (m), 720 (s) cm-1; 1 H NMR (500 MHz, CDCl3) δ7.72-7.70 (m, 2 H), 3.69 (t, J=7.2 Hz, 1 H), 3.64 (t, J=6.5 Hz, 1 H), 2.17 (br s, 1 H), 1.74-1.59 (m, 2 H), 1.46-1.40 (m, 1 H); 13 C NMR (125 MHz, CDCl3) δ169.39, 133.78, 131.96, 123.05, 62.34, 37.74, 32.03, 28.22, 22.93; high resolution mass spectrum (Cl, NH3) m/z 234.1108 ›(M+H)+; calcd for C13 H15 NO3:[234.1129].
5.0 g	With potassium carbonate In tetrahydrofuran at 20℃; for 0.166667h; Cooling with ice;	1.1 (i) Synthesis of 2-(5-hydroxypentyl)isoindole-i ,3-dione 10454] 5-Aminopentan-i-ol (i.8 g) was dissolved in tetrahydrofuran (i7 ml), potassium carbonate (i .i g) and ethyl i,3-dioxoisoindole-2-carboxylate (3.9 g) were added thereto under ice-cooling, and the mixture was stirred at room temperature for i 0 mm. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solution was filtered, and the filtrate was concentrated under reduced pressure to give the title compound (5.0 g) as a colorless liquid.10455] ‘H-NMR (400 MHz, CDC13) ö:7.82-7.87 (m, 2H),7.69-7.73 (m, 2H), 3.7i (t, J=7.2 Hz, 2H), 3.65 (t, J=6.4 Hz,2H), i.59-i.66 (m, 2H), i.42-i.47 (m, 2H)

Reference： [1]Hirschmann, Ralph; Nicolaou; Pietranico, Sherrie; Leahy, Ellen M.; Salvino, Joseph; Arison, Byron; Cichy, Maria A.; Grant Spoors; Shakespeare, William C.; Sprengeler, Paul A.; Hamley, Peter; Smith III, Amos B.; Reisine, Terry; Raynor, Karen; Maechler, Laurie; Donaldson, Cindy; Vale, Wylie; Freidinger, Roger M.; Cascieri, Margaret R.; Strader, Catherine D. [Journal of the American Chemical Society, 1993, vol. 115, # 26, p. 12550 - 12568]
[2]Current Patent Assignee: UNIVERSITY OF PENNSYLVANIA - US5552534, 1996, A
[3]Current Patent Assignee: UNIVERSITY OF PENNSYLVANIA - US5811512, 1998, A Current Patent Assignee: UNIVERSITY OF PENNSYLVANIA - US5552534, 1996, A
[4]Current Patent Assignee: UNIVERSITY OF PENNSYLVANIA - US5811512, 1998, A
[5]Current Patent Assignee: KNC LABORATORIES - US2015/336876, 2015, A1 Location in patent: Paragraph 0454; 0455

3
[ 63273-48-3 ]
[ 954-81-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; for 3h;	A solution of 5-phthalimido-1-pentanol (0.53 g, 2.3 mmol) andtriphenylphosphine (0.66 g, 2.5 mmol) in dichloromethane(25 mL) was cooled to 0 C. N-Bromosuccinimide (0.45 g,2.5 mmol) was added portion-wise over 10 min and stirring wascontinued at 0 C for 3 h. The reaction mixture diluted with dichloromethane(9 mL) and extracted with water (3 15 mL) and brine(15 mL). The organics were dried over sodium sulfate and concentratedunder reduced pressure. The residue was purified on silicagel (30% ethyl acetate/hexane) to yield the product as a clear colorlessoil (0.54 g, 1.82 mmol, 80%). 1H NMR (500 MHz, CDCl3) d 7.82(m, 2H), 7.71 (m, 2H), 3.68 (t, 2H, J = 7.5 Hz), 3.38 (t, 2H, J = 7 Hz),1.88 (m, 2H), 1.69 (m, 2H), 1.46 (m, 2H); 13C NMR (125 MHz,CDCl3) d 168.31, 133.86, 132.01, 123.13, 37.56, 33.34, 32.11,27.65, 25.31
45%	With phosphorus tribromide; In diethyl ether;	Then, 16.2 g of 5-phthalimido-1-pentanol was dissolved in 350 ml of diethyl ether, and 4.3 ml of phosphorus tribromide was added dropwise at 0 C. The reaction solution was stirred at room temperature for 9 hours and neutralized with saturated aqueous sodium hydrogen carbonate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo for removal of the solvent. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to give 9.2 g of 1-bromo-5-phthalimidopentane in a yield of 45%. Mass(m/z): 296(M+) 216 160; 1H-NMR(CDCl3): 1.44-1.55(2H,m) 1.63-1.77(2H,m) 1.86-2.00(2H,m) 3.37-3.42(2H,m) 3.67-3.73(2H,m) 7.68-7.75(2H,m) 7.81-7.88(2H,m).

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4602 - 4608
[2]Patent: US6255321,2001,B1
[3]Synthetic Communications,1985,vol. 15,p. 1277 - 1290
[4]Journal of Medicinal Chemistry,2001,vol. 44,p. 3175 - 3186

4
[ 15848-22-3 ]
[ 63273-48-3 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3175 - 3186

5
[ 38222-83-2 ]
[ 63273-48-3 ]
[ 149831-83-4 ]
[ 149831-91-4 ]
[ 149831-92-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With trifluoromethylsulfonic anhydride; In dichloromethane;	A stirred solution of 5-phthalimido-1-pentanol (III-33) (39.1 mg, 0.168 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (34.5 mg, 0.168 mmol) in dry dichloromethane (1.5 ml) was treated with triflic anhydride (28.3 ml, 0.168 mmol). After 10 min at room temperature, the mixture was diluted with water (25 ml) and extracted with dichloromethane (250 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. Sodium hydride (60percent dispersion in oil, 51 mg, 1.3 mmol) was added to a solution of alcohol III-44 (150 mg, 0.240 mmol), 5-phthalimidopentyl triflate (1.37 mmol), and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (282 mg, 1.39 mmol), in dichloromethane (1.5 ml) at 0° C. The reaction mixture was stirred for 48 h at room temperature, quenched with saturated aqueous ammonium chloride, and extracted with dichloromethane, and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (20percent ethyl acetate/petroleum ether) gave III-45 (158 mg, 78percent yield) as a colorless oil: [alpha]D25 -2.5° (c 0.36, acetonitrile); UV (2.1410-4 M, acetonitrile) lambdamax 283.6 (epsilon710), 242.4 (808) nm; IR (CHCl3) 2940 (m), 2860 (m), 1775 (m), 1715 (s), 1450 (m), 1400 (s), 1370 (s), 1175 (m), 1120 (s), 1090 (s), 1050 (s), 745 (m), 720 (s), 700 (m) cm-1; 1 H NMR (500 MHz, CDCl3) delta7.96 (d, J=8.3 Hz, 1H), 7.84-7.80 (m, 4H), 7.69-7.64 (m, 2H), 7.50-7.17 (m, 12H), 4.69 (d, J=11.0 Hz, 1H), 4.67 (s, 2H), 4.64 (d, J=11.0 Hz, 1H), 4.36 (d, J=7.7 Hz, 1H), 4.21-4.17 (m, 1H), 3.86-3.81 (m, 1H), 3.66 (t, J=7.3 Hz, 2H), 3.60-3.39 (m, 6H), 3.28 (dd, J=7.8, 8.8 Hz, 1H), 3.00 (t, J=6.7 Hz, 2H), 2.12 (dd, J=5.4, 12.2 Hz, 1H), 1.71-1.58 (m, 5H), 1.47-1.36 (m, 3H); 13 C NMR (125 MHz, CDCl3) delta168.37, 138.61, 138.31, 135.19, 133.83, 133.56, 132.13, 131.03, 129.11, 128.31, 128.19, 127.96, 127.63, 127.51, 127.44, 126.65, 124.68, 123.51, 123.12, 119.78, 119.49, 113.70, 103.85, 82.83, 78.23, 74.90, 73.10, 72.16, 71.39, 70.95, 68.68, 37.86, 33.94, 29.67, 29.11, 28.36, 25.75, 23.41; high resolution mass spectrum (FAB, m-nitrobenzyl alcohol) m/z 865.3201 [(M+Na)+; calcd for C49 H50 N2 O9 SNa: 865.3134].

Reference： [1]Patent: US5552534,1996,A

6
[ 38222-83-2 ]
[ 2508-29-4 ]
[ 22509-74-6 ]
[ 63273-48-3 ]
[ 149831-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane; benzene;	A. 5-Phthalimido-1-pentyl triflate (15). To a solution of 5-aminopentanol (42.7 mmol) in benzene (100 mL) is added N-carbethoxyphthalimide (10.3 g, 47.0 mmol). The solution is stirred at room temperature for 5 h. The solvent is removed in vacuo to provide an oil, which is purified by flash chromatography. To a solution of 5-phthalimido-1-pentanol (22.2 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 5-phthalimido-1-pentyl triflate (15) which is used without further purification.

Reference： [1]Patent: US5550251,1996,A

7
[ 38222-83-2 ]
[ 63273-48-3 ]
[ 149831-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoromethylsulfonic anhydride; In dichloromethane;	L. 5-Phthalimido-1-O-trifluoromethanesulfonylpentanol To a solution of 5-phthalimido-1-pentanol (39.1 mg, 0.168 mmol) in dry dichloromethane (1.5 mL) was added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (34.5 mg, 0.168 mmol) followed by triflic anhydride (28.3 mug, 0.168 mmol). The solution was stirred at room temperature for 10 minutes. The reaction was poured into water (25 mL) and extracted with dichloromethane (2*50 mL). The organic layer was washed with a saturated sodium chloride solution and dried with anhydrous sodium sulfate. The solvents were removed under reduced pressure to yield a pale yellow solid which was used immediately without further purification.

Reference： [1]Patent: US5811512,1998,A

8
[ 38222-83-2 ]
[ 63273-48-3 ]
[ 149831-84-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With trifluoromethylsulfonic anhydride; In dichloromethane;	A stirred solution of 5-phthalimido-1-pentanol (III-33) (1.32 g, 4.67 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.960 g, 4.67 mmol) in dry dichloromethane (10 ml) was treated with triflic anhydride (0.784 ml, 4.67 mmol). After 10 min at room temperature, the mixture was diluted with water (100 ml) and extracted with dichloromethane (2200 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. Sodium hydride (60percent dispersion in oil, 0.20 g, 5.06 mmol) was added to a solution of alcohol III-32 (1.27 g, 3.89 mmol), 5-phthalimdopentyl triflate (4.67 mmol), and 15-crown-5 (20 mg, 2.3 mol percent), in dichloromethane (100 ml) at 0° C. After stirring for 24 h at room temperature, the mixture was poured into water. The aqueous layer was extracted with dichloromethane (350 ml) and the combined extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography (3percent ether/dichloromethane) provided III-34 (1.82 g, 86percent yield) as a colorless oil: [alpha]D25 -8.2° (c 0.70, CHCl3); IR (CHCl3) 3080 (w), 3020 (m), 3009 (m), 2959 (m), 2880 (m), 1780 (m), 1719 (s), 1652 (m), 1500 (w), 1470 (w), 1457 (m), 1440 (m), 1400 (s), 1365 (m), 1235 (m), 1110 (br, s), 1058 (br, s), 908 (w), 692 (m), cm-1; 1 H NMR (500 MHz, CDCl3) delta7.80 (m, 2H), 7.68 (m, 2H), 7.25-7.34 (m, 10H), 6.38, (dd, J=6.1, 1.2 Hz, 1H), 4.84 (m, 2H), 4.66 (d, J=11.4 Hz, 1H), 4.63 (d, J=11.7 Hz, 1H), 4.55 (d, J=11.7 Hz, 1H), 4.19 (m, 1H), 4.00 (m, 1H), 3.81 (dd, J=8.7, 6.2 Hz, 1H), 3.64-3.74 (m, 4H), 3.40-3.50 (m, 2H), 1.60-1.70 (m, 4H), 1.40 (m, 2H); 13 C NMR (62.9 MHz, CDCl3) delta168.4, 144.8, 138.4, 138.3, 133.9, 132.2, 128.4, 127.9, 127.8, 127.6, 123.2, 99.9, 76.8, 75.8, 74.5, 73.8, 71.4, 70.5, 69.2, 37.9, 29.2, 28.5, 23.5; high resolution mass spectrum (Cl, NH3) m/z 541.2483 (M+; calcd for C33 H35 NO6: 541.2464).

Reference： [1]Patent: US5552534,1996,A

9
[ 38222-83-2 ]
15-crown-S [ No CAS ]
[ 63273-48-3 ]
[ 149831-84-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With trifluoromethylsulfonic anhydride; In dichloromethane;	AG. 3,4-Di-O-Benzyl-6-O-(5-phthalimidopentyl)-D-glucal (III-34) 5-Phthalimidopentyl triflate was prepared as follows: A stirred solution of 5-phthalimido-1-pentanol (III-33) (1.32 g, 4.67 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.960 g, 4.67 mmol) in dry dichloromethane (10 ml) was treated with triflic anhydride (0.784 ml, 4.67 mmol). After 10 min at room temperature, the mixture was diluted with water (100 ml) and extracted with dichloromethane (2200 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. Sodium hydride (60percent dispersion in oil, 0.20 g, 5.06 mmol) was added to a solution of alcohol III-32 (1.27 g, 3.89 mmol), 5-phthalimdopentyl triflate (4.67 mmol), and 15-crown-S (20 mg, 2.3 mol percent), in dichloromethane (100 ml) at 0° C. After stirring for 24 h at room temperature, the mixture was poured into water. The aqueous layer was extracted with dichloromethane (350 ml) and the combined extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography (3percent ether/dichloromethane) provided III-34 (1.82 g, 86percent yield) as a colorless oil: [alpha]D25 -8.20 (c 0.70, CHCl3); IR (CHCl3) 3080 (w), 3020 (m), 3009 (m), 2959 (m), 2880 (m), 1780 (m), 1719 (s), 1652 (m), 1500 (w), 1470 (w), 1457 (m), 1440 (m), 1400 (s), 1365 (m), 1235 (m), 1110 (br, s), 1058 (br, s), 908 (w), 692 (m), cm-1; 1 H NMR (500 MHz, CDCl3) delta7.80 (m, 2 H), 7.68 (m, 2 H), 7.25-7.34 (m, 10 H), 6.38, (dd, J=6.1, 1.2 Hz, 1 H), 4.84 (m, 2 H), 4.66 (d, J=11.4 Hz, 1 H), 4.63 (d, J=11.7 Hz, 1 H), 4.55 (d, J=11.7 Hz, 1 H), 4.19 (m, 1 H), 4.00 (m, 1 H), 3.81 (dd, J=8.7, 6.2 Hz, 1 H), 3.64-3.74 (m, 4 H), 3.40-3.50 (m, 2 H), 1.60-1.70 (m, 4 H), 1.40 (m, 2 H); 13 C NMR (62.9 MHz, CDCl3) delta168.4, 144.8, 138.4, 138.3, 133.9, 132.2, 128.4, 127.9, 127.8, 127.6, 123.2, 99.9, 76.8, 75.8, 74.5, 73.8, 71.4, 70.5, 69.2, 37.9, 29.2, 28.5, 23.5; high resolution mass spectrum (Cl, NH3) m/z 541.2483 (M+; calcd for C33 H35 NO6: 541.2464).

Reference： [1]Patent: US5811512,1998,A

10
[ 15223-20-8 ]
[ 63273-48-3 ]
C₁₄H₁₄F₃NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [bis(acetoxy)iodo]benzene; In dichloromethane; at 20℃; for 16h;Inert atmosphere; Irradiation;	General procedure: An oven-dried microwave tube equipped with a stirring bar under argon was charged with PIDA (296 mg, 0.9 mmol, 2.3 equiv.),freshly distilled degassed CH2Cl2 (3 mL), I (102 mg, 0.4 mmol, 1equiv.) followed by 1 (2 mmol, 5 equiv.). The mixture was stirred at20 C for 16 h under irradiation with a blue LED (450e455 nm)placed 5 cm away. a,a,a-Trifluoroacetophenone (56 mL, 0.4 mmol, 1equiv.) was added as an internal standard. The reaction volume was halved via argon bubbling and acetyl chloride (3.9 mL, 56 mmol,135 equiv.) was added. The mixture was stirred at 20 C for 10 min. Upon full conversion by TLC, the crude mixturewas poured onto an ice-cold saturated solution of NaHCO3 (100 mL). The aqueous layerwas extracted with CH2Cl2 (3 30 mL). The combined organiclayers were washed with brine (70 mL), dried over Na2SO4,concentrated under vacuum and purified by flash column chromatographyto afford the desired product 3.

Reference： [1]Tetrahedron,2020,vol. 76

11
[ 136918-14-4 ]
[ 2508-29-4 ]
[ 63273-48-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With Iron(III) nitrate nonahydrate In toluene at 110℃; for 24h; Inert atmosphere;	4.2.4. Procedure for the synthesis of 5-phthalimido-1-pentanol 1i 5-Phthalimido-1-pentanol 1i was synthesized following the literature [21]. A round-bottom flask, equipped with a condenser,under argon, was charged with 5-aminopentanol (1 mL, 9 mmol, 1equiv.), phthalimide (2.2 g, 15.3 mmol, 1.7 equiv.) and toluene(9 mL). Iron-(III) nitrate nonahydrate (181.8 mg, 0.45 mmol, 0.05equiv.) was added and the reaction mixture was stirred at 110 C for24 h. The reaction mixture was filtered over celite and the solvent was evaporated under vacuum. The crude mixture was purified byflash column chromatography (height: 20 cm, width: 4 cm, CH2Cl2/EtOAc 90/10) to afford 1i as a colorless oil (1.3 g, 5.4 mmol, 60%).

Reference： [1]Barday, Manuel; Blieck, Remi; Ruyet, Louise; Besset, Tatiana [Tetrahedron, 2020, vol. 76, # 51]

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[ CAS No. 63273-48-3 ] {[proInfo.proName]}

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[ 63273-48-3 ] Synthesis Path-Upstream 1~2

[ 63273-48-3 ] Synthesis Path-Downstream 1~11

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