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[ CAS No. 532-24-1 ]

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Chemical Structure| 532-24-1
Chemical Structure| 532-24-1
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CAS No. :532-24-1 MDL No. :MFCD00005549
Formula : C8H13NO Boiling Point : 217.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :139.19 g/mol Pubchem ID :79038
Synonyms :

Safety of [ 532-24-1 ]

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

Application In Synthesis of [ 532-24-1 ]

  • Upstream synthesis route of [ 532-24-1 ]
  • Downstream synthetic route of [ 532-24-1 ]

[ 532-24-1 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 532-24-1 ]
  • [ 87571-88-8 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 25, p. 4257 - 4259
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 11, p. 3756 - 3767
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  • [ 87571-88-8 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 23, p. 3977 - 3980
[2] Journal of the American Chemical Society, 1957, vol. 79, p. 4194[3] Journal of the American Chemical Society, 1958, vol. 80, p. 4677
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4474 - 4488
[5] Organic Process Research and Development, 2003, vol. 7, # 2, p. 209 - 213
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  • [ 532-24-1 ]
  • [ 87571-88-8 ]
  • [ 81487-04-9 ]
Reference: [1] Organic Process Research and Development, 2003, vol. 7, # 2, p. 209 - 213
  • 4
  • [ 532-24-1 ]
  • [ 100-39-0 ]
  • [ 28957-72-4 ]
Reference: [1] Patent: EP1726590, 2006, A1, . Location in patent: Page/Page column 55
  • 5
  • [ 532-24-1 ]
  • [ 28957-72-4 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 29, p. 5007 - 5011
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 515 - 518
  • 6
  • [ 100371-46-8 ]
  • [ 36127-17-0 ]
  • [ 532-24-1 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 29, p. 5357 - 5360
  • 7
  • [ 532-24-1 ]
  • [ 616-38-6 ]
  • [ 36127-17-0 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 1, p. 13 - 19
  • 8
  • [ 532-24-1 ]
  • [ 541-41-3 ]
  • [ 32499-64-2 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In tolueneReflux In a dry 500 mL round-bottom flask was added a stir-bar, 3-tropinone (10.0 g, 0.072 mol) and K2CO3 (0.050 g). Anhydrous toluene (90 mL) was added followed by 3 equiv of ethylchloroformate (21 mL, 0.22 mol) via syringe, drop wise. The flask was fitted with a condenser, nitrogen bubbler and heated to reflux overnight with stirring. The mixture was concentrated under vacuum and the brown oil was dissolved in CH2Cl2 (100 mL) and washed with H2O (100 mL). The layers were separated in a separatory funnel and the aqueous layer extracted with CH2Cl2 (3 .x. 50 mL). The organics were combined and dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by column chromatography (SiO2, EtOAc/hexane, 1:3) to afford 14 (13.1 g, 92percent) as a light yellow oil. 1H NMR: δ 4.51 (br s, 2H), 4.16 (q, J = 7.2 Hz, 2H), 2.63 (br s, 2H), 2.31 (dd, J = 17.4, 1.6 Hz, 2H), 2.07-2.03 (m, 2H), 1.65 (d, J = 7.6 Hz, 2H), 1.25 (t, J = 7.2 Hz, 3H). 13C NMRδ 208.3, 154.1, 61.6, 53.2, 49.1, 29.5(2), 28.8(2), 14.9.
90% for 5 h; Reflux The 2.78g (20mmol) tropinone dissolved in toluene solvent, was added slowly with a syringe 5ml of ethyl chloroformate, reflux, after 5 hours, the reaction was complete tropinone materials. The solvent was distilled off, washed three times with water, extracted three times with ethyl acetate. The combined extracts were washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent removed to give a pale yellow liquid yield of about 90percent
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 4, p. 629 - 632
[2] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 4, p. 569 - 574
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 24, p. 7551 - 7558
[4] Patent: CN105294674, 2016, A, . Location in patent: Paragraph 0147; 0148; 0149
[5] Patent: WO2018/140876, 2018, A1, . Location in patent: Page/Page column 216
[6] Tetrahedron Letters, 1996, vol. 37, # 9, p. 1463 - 1466
[7] Journal of Medicinal Chemistry, 1988, vol. 31, # 2, p. 433 - 444
[8] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 24, p. 6865 - 6868
[9] European Journal of Pharmacology, 1997, vol. 321, # 2, p. 189 - 194
[10] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 19, p. 2699 - 2704
[11] Journal of Medicinal Chemistry, 2008, vol. 51, # 19, p. 6095 - 6109
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  • [ 76272-36-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 1984, vol. 19, # 2, p. 105 - 110
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  • [ 25602-68-0 ]
YieldReaction ConditionsOperation in experiment
43%
Stage #1: With carbonochloridic acid 1-chloro-ethyl ester In 1,2-dichloro-ethane at 20℃;
Stage #2: at 20℃; for 1 h;
Tropinone (10.0 g; 71.84 mmol) was dissolved in DCE (60 mL) and treated drop-wisewith 1-chloroethyl chloroformate ACE-C1 (14.5 mL; 19.11 g; 133.7 mmol). The reaction wasallowed to stir at room temperature overnight and was then diluted with Et20 (400 mL) andfiltered. The filtrate was concentrated under reduced pressure to provide the crude chloroethylcarbamate. This compound was taken in MeOH (200 mL) and stirred at room temperature for 1h, then concentrated under reduced pressure (at 55°C) to provide the crude des-methyltropinoneas the HC1 salt (tan solid, 11.4 g, 98percent yield). The crude material was recrystallized fromacetonitrile to furnish the pure product as a white crystalline solid (5 g, 43percent yield). *H NMR(400 MHz, DMSO-d6) 8 1.79 (dd, J= 15.0, 6.9 Hz, 2H), 2.09 (m, 2H), 2.40 (d, J= 16.7 Hz,2H), 3.02 (dd, J= 17.1, 4.3 Hz, 2H), 4.23 (s, 2H), 10.00 (br s, 2H)Des-methyl tropinone (5.10 g; 31.55 mmol) was dissolved in CH2CI2 (50 mL) and treated withbenzyl chloroformate (4.29 mL; 5.11 g; 29.98 mmol) DIPEA (16.48 mL; 12.23 g; 94.66 mmol)was added drop-wise (exothermic reaction). The resulting clear solution was allowed to stir atroom temperature for 30 min and was subsequently diluted with 100 mL CH2CI2. The organicphase was washed with 1 N HC1 (2 x 100 mL), dried on Na2SC>4 and concentrated to provide thecrude product (7.2 g, 88percent yield). *H NMR (400 MHz, CDC13) 8 1.71 (dd, J= 15.0, 7.2 Hz, 2H),2.12 (m, 2H), 2.38 (d, J= 15.9 Hz, 2H), 2.67 (m, 2H), 4.62 (s, 2H), 5.22 (s, 2H), 7.38 (m, 5H).
Reference: [1] Patent: WO2006/23852, 2006, A2, . Location in patent: Page/Page column 84
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 10, p. 1817 - 1820
[3] Patent: WO2010/126163, 2010, A1, . Location in patent: Page/Page column 38
[4] Patent: WO2007/100670, 2007, A1, . Location in patent: Page/Page column 47
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  • [ 25602-68-0 ]
Reference: [1] Patent: WO2004/100946, 2004, A1, . Location in patent: Page 77
  • 12
  • [ 532-24-1 ]
  • [ 501-53-1 ]
  • [ 130753-13-8 ]
YieldReaction ConditionsOperation in experiment
55% With potassium carbonate In toluene for 2 h; Reflux Example 1: Synthesis of benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (compoundI); -To a stirred solution of 8-methyl-8-azabicyclo[3.2.1]octan-3-one (200.0 g, 143 mmol) and K2CO3 (1.19 g) in toluene (4.0 L) was added benzyl chloroformate (1.96 L, 572 mmol, 50percent in toluene) at room temperature and the resulting solution was stirred at reflux for 2 h. Reaction mixture was cooled to room temperature and then treated with ice-cold water (2.0 L). The organic phase was separated and the aqueous phase extracted with ethyl acetate (2.0 L x 2). Organic phases were combined, dried over anhydrous sodium sulphate, filtered and evaporated to give a residue, which was purified by vacuum distillation. Yield: 215.0 g (55percent). TLC, Rf (Hexane/Ethyl Acetate 30percent) = 0.3. IR cm"1 (CHCl3) 2959, 2887, 1702, 1414, 1367, 1338, 1320, 1284, 1156, 1004, 738. 1HNMR (400 MHz, CDCl3): δ 7.32 (m, 5H), 5.19 (s, 2H), 4.59 (br s, 2H), 2.72-2.56 (m, 2H), 2.34 (m, 2H), 2.1 (m, 2H), 1.68 (m, 2H). MS: 258 (M-I).
Reference: [1] Patent: WO2011/18796, 2011, A1, . Location in patent: Page/Page column 19
[2] Journal of Organic Chemistry, 2008, vol. 73, # 22, p. 9016 - 9021
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  • [ 24424-99-5 ]
  • [ 532-24-1 ]
  • [ 185099-67-6 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With carbonochloridic acid 1-chloro-ethyl ester In 1,2-dichloro-ethane at 80℃; for 5 h;
Stage #2: at 75℃; for 1.5 h;
Stage #3: With sodium hydroxide In water at 20℃;
3-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic Acid tert-butyl Ester
A mixture of 8-methyl-8-aza-bicyclo[3.2.1]octan-3-one (50.5 g, 359 mmol) and 1-chloroethyl chloroformate (117 mL, 1.08 mol) in CH2ClCH2Cl (500 mL) was heated to 80° C. for 5 h.
The mixture was allowed to cool to rt, and the solvents were removed under reduced pressure.
The residue was dried under high vacuum for 3 h, and was added in portions to MeOH (250 mL) over 30 min.
The mixture was stirred at 75° C. for 1 h, and allowed to cool to rt.
The solvents were removed under reduced pressure.
The residue was diluted with Et2O (250 mL), and the mixture was sonicated for 15 min.
The mixture was then stirred for 30 min, and filtered.
The precipitate was washed with Et2O (125 mL), and dried under high vacuum.
The residue was diluted with dioxane (400 mL), and the mixture was cooled to 0° C. Aq. 1M NaOH (400 mL) was added. Boc2O (82.3 g, 377 mmol) was added, and the mixture was stirred overnight while warming up to rt.
The mixture was extracted with Et2O (2*).
The combined org.
extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure.
Purification of the crude by FC (EtOAc/heptane 3:7) yielded the title compound (59.0 g, 73percent). LC-MS: tR=0.83 min.
Reference: [1] Patent: US2009/176823, 2009, A1, . Location in patent: Page/Page column 28
[2] Chemistry - A European Journal, 2013, vol. 19, # 1, p. 82 - 86
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  • [ 50893-53-3 ]
  • [ 24424-99-5 ]
  • [ 532-24-1 ]
  • [ 185099-67-6 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: at 80℃; for 5 h;
Stage #2: at 20 - 75℃; for 1.5 h;
3-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester. A mixture of 8-methyl-8-aza-bicyclo[3.2.1]octan-3-one (50.5 g, 359 mmol) and 1- chloroethyl chloroformate (117 mL, 1.08 mol) in CH2ClCH2Cl (500 mL) was heated to 80 0C for 5 h. The mixture was allowed to cool to rt, and the solvents were removed under reduced pressure. The residue was dried under high vacuum for 3 h, and was added in portions to MeOH (250 mL) over 30 min. The mixture was stirred at 75 0C for 1 h, and allowed to cool to rt. The solvents were removed under reduced pressure. The residue was diluted with Et2O (250 mL), and the mixture was sonicated for 15 min. The mixture was then stirred for 30 min, and filtered. The precipitate was washed with Et2O (125 mL), and dried under high vacuum. The residue was diluted with dioxane (400 mL), and the mixture was cooled to 0 0C. Aq. IM NaOH (400 mL) was added. BoC2O (82.3 g, 377 mmol) was added, and the mixture was stirred overnight while warming up to rt. The mixture was extracted with Et2O (2x). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtO Ac/heptane 3:7) yielded the title compound (59.0 g, 73percent). LC-MS: tR = 0.83 min.
Reference: [1] Patent: WO2007/88514, 2007, A1, . Location in patent: Page/Page column 75-76
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  • [ 532-24-1 ]
  • [ 185099-67-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 21, p. 5281 - 5284
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 515 - 518
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3597 - 3600
[4] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 10, p. 1817 - 1820
[5] Tetrahedron, 2002, vol. 58, # 28, p. 5669 - 5674
[6] Patent: EP1726590, 2006, A1,
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  • [ 185099-68-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 10, p. 1817 - 1820
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