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[ CAS No. 883-44-3 ]

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Chemical Structure| 883-44-3
Chemical Structure| 883-44-3
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CAS No. :883-44-3 MDL No. :MFCD00023097
Formula : C11H11NO3 Boiling Point : 376.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :205.21 g/mol Pubchem ID :70160
Synonyms :

Safety of [ 883-44-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 883-44-3 ]

  • Upstream synthesis route of [ 883-44-3 ]
  • Downstream synthetic route of [ 883-44-3 ]

[ 883-44-3 ] Synthesis Path-Upstream   1~17

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YieldReaction ConditionsOperation in experiment
85.1% for 0.5 h; Reflux 5.0mmol N-(3-hydroxypropyl) phthalimide, 5.00mmol PBr3The refluxing reaction was completed for 0.5 h, and was detected by TLC. After cooling, it was poured into ice water to precipitate a solid. The crude product was recrystallized from anhydrous ethanol to obtain white solid N-(3-bromopropyl)phthalimide (1.14 g). Mp71-73°C, yield 85.1percent.
Reference: [1] Chemical Communications, 2003, # 2, p. 260 - 261
[2] Tetrahedron Letters, 2003, vol. 44, # 44, p. 8143 - 8147
[3] Patent: CN107540647, 2018, A, . Location in patent: Paragraph 0045-0048
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YieldReaction ConditionsOperation in experiment
100% at 125℃; for 6.5 h; Inert atmosphere 3-Aminopropan-1-ol (10.0 g, 133.1 mmol) was dissolved in anhydrous toluene (100 ml). Phthalic anhydride (19.7 g, 133.1 mmol) was added and the reaction mixture was heated to 125 °C with stirring, under an atmosphere of argon for 6.5 h. After cooling to rt, the solvent was evaporated in vacuo to give phthalimide 5 (31.7 g, quantitative) as a white powder that required no further purification.
90% With o-phthalimide-N-sulfonic acid In ethanol at 80℃; for 2 h; Green chemistry General procedure: A mixture of phthalic anhydride (0.296 g, 2 mmol), amine (2.2 mmol), and phthalimide-N-sulfonic acid (0.091 g, 20 molpercent) in ethanol (5 ml) was stirred for 3 h at 80 °C. After completion (monitored by TLC), the insoluble catalyst was separated by filtration, washed with acetone, and dried (weight: 0.090 g, 99 percent recovered). The organic layer was concentrated under reduced pressure to give the desired product, washed with water, and recrystallized in ethanol (each product was dissolved in a minimum amountof hot ethanol and allowed to reach gradually to room temperature). In addition, some products needed extrapurification step by small column chromatography using the CH2Cl2/n-hexane solvent mixture (50:50).
87% With triethylamine In toluene for 24 h; Reflux Step 1To a solution of 3 -aminopropan- 1 -ol ( 1.0 g, 13.1 mmol) and isobenzofuran- 1 ,3 -dione (2.0 g,13.1 mmol) in toluene (25 mL, 3 mL/mmol) was added Et3N (2 mL, 13.1 mmol) and the reaction was heated at reflux for 24 h. Then reaction was quenched with water and extracted with EtOAc (2 x 40 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford 2-(3-hydroxypropyl)isoindo line- 1,3- dione (1.8 g, 87percent). Observed mass (M+l): 206.1. This material was taken to the next step without further purification
80.2% for 1 h; Reflux 0.013mol phthalic anhydride in the three-neck flask, 0.013mol propanolamine was added dropwise at room temperature, the reaction was refluxed for 1.0H, cooled and the precipitated solid was recrystallized to give a white solid N- (3- hydroxypropyl) phthalimido imine 2.14g,
79% for 4 h; Reflux; Inert atmosphere 2-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4- d][l,3]dioxol-4-yl)meth l)(methyl)amino)propyl)isoindoline-l,3-dioneStep 1. Preparation of 2-(3-hydroxypropyl)isoindoIine-l,3-dioneTo a solution of isobenzofuran-l ,3-dione (10.0 g, 135.1 mmol) in toluene (250 mL) was added 3-amino-l -propanol (10.0 g, 67.6 mmol) and the mixture was heated to reflux for 4 h under N2. The mixture was concentrated and water was added. The mixture was extracted with EA (100 mL x4). The organic phase was dried with Na2S04 and concentrated to afford 2-(3-hydroxypropyl)isoindoline-l ,3-dione (1 1.0 g, 79percent) as white solid. 1H NMR (500 MHz, CDC13): δ 7.84-7.87 (m, 2H), 7.72-7.75 (m, 2H), 3.85-3.88 (m, 2H), 3.61 -3.63 (m, 2H), 2.42 (brs, 1H), 1.86-1.9 (m, 2H) ppm. MS (ESI): m/z 206.7 [M+l]+.

Reference: [1] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 644 - 647
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 32, p. 6094 - 6104
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 16, p. 5903 - 5914
[4] Chemistry - A European Journal, 2014, vol. 20, # 44, p. 14256 - 14260
[5] Chemical Papers, 2017, vol. 71, # 11, p. 2293 - 2299
[6] Patent: WO2011/103196, 2011, A1, . Location in patent: Page/Page column 110-111
[7] Patent: CN107540647, 2018, A, . Location in patent: Paragraph 0042-0044
[8] Patent: WO2012/82436, 2012, A2, . Location in patent: Page/Page column 245
[9] Organic Letters, 2013, vol. 15, # 4, p. 917 - 919
[10] Journal of the American Chemical Society, 2015, vol. 137, # 2, p. 807 - 819
[11] Tetrahedron, 2003, vol. 59, # 45, p. 8877 - 8888
[12] Atti della Accademia delle Scienze di Torino, Classe di Scienze Fisiche, Matematiche e Naturali, 1933, vol. 9, p. 358,362
[13] Tetrahedron Letters, 2002, vol. 43, # 27, p. 4747 - 4751
[14] Journal of Medicinal Chemistry, 2004, vol. 47, # 10, p. 2411 - 2413
[15] Journal of the American Chemical Society, 2006, vol. 128, # 12, p. 4023 - 4034
[16] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 649 - 664
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YieldReaction ConditionsOperation in experiment
100% With triphenylphosphonium ruthenium chloride; C29H30NOPRu; hydrogen; sodium carbonate In ethanol; toluene at 25℃; for 24 h; Autoclave In a 10 ml reaction tube, adding phosphine nitrogen ligand L10a (0.35 mg, 0 . 65 μmol) with the three-phenyl phosphorus is great (0.48 mg, 0 . 50 μmol), system through the vacuum line, replace the nitrogen 3 times, and steams newly added new degassed toluene 2 ml, solution in 90 °C under stirring 3 hours, cooling to room temperature, solvent is removed under reduced pressure. At the same time in another 10 ml hydrogenation bottle, adding β - aminoketone laq (40.6 mg, 0.2 mmol) with anhydrous sodium carbonate (2.12 mg, 0 . 02 mmol), system through the vacuum line, replace the nitrogen 3 times. A syringe has been coordination of the new catalyst for steaming and new degassing of ethanol (3 ml) containing dissolved out and injected into the substrate and additive in the reaction tube, the reaction system is put in an autoclave, in 25 °C and H2(50 Bar) is stirred under the condition 24 hours, the solvent is removed under reduced pressure, taking a small amount of the mixed system is nuclear magnetic resonance to determine the conversion rate. The rest of the survivor column chromatography separation, to obtain the pure product 2 aq. The conversion is 100percent, enantiomeric excess is 92percent. 2 Aq: white solid. According to the embodiment 1 - 12 and not the result of the symmetrical field of catalytic hydrogenation of the well known common sense, can without any doubt be inferred in this embodiment of the product structure is shown in formula (II) of the structure.
Reference: [1] Patent: CN105085372, 2018, B, . Location in patent: Paragraph 0123; 0124
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YieldReaction ConditionsOperation in experiment
93% With dipotassium peroxodisulfate In water at 100℃; for 0.166667 h; Microwave irradiation; Green chemistry General procedure: Amide (1.0 mmol), amine (1.0 mmol) and K2S2O8 (1.5 mmol) were charged in microwave vial added water (2.0 mL), the reaction mixture was treated at 100°C and 100W for 10 min. After the complete conversion (by TLC) of the amine, distilled water (10 mL) was added and extracted with ethyl acetate (2 ×10 mL). The combined organic phase was dried over Na2SO4, and then concentrated using rotary vacuum evaporator. The crude product was purified by column chromatography (30percent Ethyl acetate/hexane) to get pure compound.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 33, p. 4775 - 4779
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YieldReaction ConditionsOperation in experiment
95% With t-butyl bromide In acetonitrile for 1.5 h; Reflux General procedure: To asolution of the PMB ether (1 mmol) in acetonitrile (10 mL), t-BuBr (1.1 equiv)was added and stirred at reflux. After completion of the reaction (monitored byTLC), it was concentrated under reduced pressure and the resulting crude wasdissolved in ethyl acetate (50 mL) and washed with saturated sodiumhydrogenocarbonate (25 mL). The aqueous layer was extracted with ethylacetate (2 5 mL) and the combine organic layer was washed with brinesolution, dried (MgSO4), concentrated under reduced pressure and the residuewas purified by column chromatography (silica gel, EtOAc, cyclohexane) toafford the corresponding alcohol.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 49, p. 6823 - 6826
[2] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9227 - 9235,9
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Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 24, p. 3919 - 3920
[2] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 10, p. 1649 - 1658
[3] Journal of the American Chemical Society, 1931, vol. 53, p. 2763,2767
[4] Journal of the American Chemical Society, 1988, vol. 110, p. 5779
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Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 4, p. 706 - 721
[2] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1639 - 1645
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Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 1, p. 292 - 295[2] Angew. Chem., 2018, vol. 130, # 1, p. 298 - 301,4
[3] Patent: US6201016, 2001, B1,
[4] Patent: US5681966, 1997, A,
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YieldReaction ConditionsOperation in experiment
24% With potassium carbonate In N,N-dimethyl-formamide (e)
Preparation of N-(3-hydroxypropyl)phthalimide (106).
A mixture of 3-bromopropanol (4 g, 0.029 mol), potassium phthalate (8 g, 0.043 mol) and potassium carbonate (4 g, 0.029 mol) in dry DMF (50 ml) was stirred and heated at 70° C. for four hours.
The mixture was diluted with water (100 ml) and extracted with ethyl acetate (3*75 ml).
The organic extract was washed with water (3*100 ml) and dried (Na2 SO4).
Removal of the solvent under reduced pressure left a white solid which was extracted with benzene.
The benzene extract was evaporated to a white solid and recrystallized from ethyl acetate-hexanes to give white crystals (1.27 g, 24percent).
Reference: [1] Patent: US5681966, 1997, A,
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Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 22, p. 7029 - 7043
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  • [ 201230-82-2 ]
  • [ 5022-29-7 ]
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Reference: [1] ChemSusChem, 2018, vol. 11, # 14, p. 2310 - 2314
  • 12
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Reference: [1] Patent: US4652573, 1987, A,
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  • [ 88-99-3 ]
  • [ 156-87-6 ]
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 44, p. 14256 - 14260
  • 14
  • [ 5428-09-1 ]
  • [ 883-44-3 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 16, p. 4979 - 4983
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Reference: [1] Chemische Berichte, 1905, vol. 38, p. 633,2389
[2] Chemische Berichte, 1890, vol. 23, p. 89
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YieldReaction ConditionsOperation in experiment
100% With 2-iodoxybenzoic acid In ethyl acetate for 2 h; Reflux Step 2. Preparation of 3-(l,3-dioxoisoindolin-2-yl)propanal A mixture of 2-(3-hydroxypropyl)isoindoline-l,3-dione (2.0 g, 8.76 mmol) and IBX (8.2 g, 29.27 mmol) in 60 mL EA was refluxed for 2 h. The mixture was filtered and filtrate was concentrated to afford 3-(l,3-dioxoisoindolin-2-yl)propanal (2.0 g , yield: 100percent) as white solid. NMR (500 MHz, CDC13): δ 9.82 (s, 2H), 7.84-7.86 (m, 2H), 7.72-7.74 (m, 2H), 4.04 (t, J = 7.0 Hz, 2H), 2.87-2.89 (m, 2H) ppm. MS (ESI): m/z 553.7 [M+l]+.
38% With N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate In chloroform; water at 20℃; for 4.5 h; A 50 ml round bottom flask was charged with aq. NaHCO3(0.05 M, 10 ml), aq. K2CO3(0.5 M, 10 ml) and CHCl3(5 ml). Alcohol 5 (16.02 g, 78.1 mmol) was dissolved in CHCl3(50 ml) and transferred to the reaction mixture followed by tetra-nbutylammonium chloride (4.34 g, 15.6 mmol), N-chlorosuccinimide (20.9 g, 156.1 mmol) and TEMPO (2.44 g, 15.6 mmol) and the reaction mixture was stirred vigorously at rt for 4.5 h. The phases were separated and the organic phase was washed with sulfate buffer (100 ml), NaHCO3(100 ml), and brine (100 ml), dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash column chromatography (35percent EtOAc in n-heptane, v/v) gave aldehyde 9 (6.54 g, 38percent) as a white amorphous solid.
Reference: [1] Patent: WO2012/82436, 2012, A2, . Location in patent: Page/Page column 245-246
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 32, p. 6094 - 6104
[3] Journal of the American Chemical Society, 2006, vol. 128, # 12, p. 4023 - 4034
[4] Tetrahedron, 2002, vol. 58, # 9, p. 1719 - 1737
[5] Helvetica Chimica Acta, 2005, vol. 88, # 10, p. 2610 - 2616
[6] Journal of Organic Chemistry, 1989, vol. 54, # 22, p. 5387 - 5390
[7] Organic Letters, 2003, vol. 5, # 17, p. 3115 - 3118
[8] Green Chemistry, 2012, vol. 14, # 5, p. 1493 - 1501
[9] Journal of the American Chemical Society, 2013, vol. 135, # 24, p. 9083 - 9090
[10] Tetrahedron, 2003, vol. 59, # 45, p. 8877 - 8888
[11] Journal of Medicinal Chemistry, 1999, vol. 42, # 4, p. 706 - 721
[12] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 10, p. 2609 - 2624
[13] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13121 - 13140
[14] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 644 - 647
[15] Journal of the American Chemical Society, 1988, vol. 110, p. 5779
[16] Tetrahedron Letters, 1993, vol. 34, # 24, p. 3919 - 3920
[17] Journal of Medicinal Chemistry, 2004, vol. 47, # 10, p. 2411 - 2413
[18] Patent: US2006/84687, 2006, A1, . Location in patent: Page/Page column 22
[19] Patent: US2005/119332, 2005, A1,
[20] Organic Letters, 2009, vol. 11, # 11, p. 2465 - 2468
[21] Patent: WO2012/82436, 2012, A2, . Location in patent: Page/Page column 223-224
[22] Patent: WO2012/82436, 2012, A2, . Location in patent: Page/Page column 265-266
[23] Chemistry - A European Journal, 2013, vol. 19, # 20, p. 6213 - 6216
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Reference: [1] Patent: US2002/2199, 2002, A1,
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