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Chemical Structure| 85908-96-9
Chemical Structure| 85908-96-9
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Product Details of [ 85908-96-9 ]

CAS No. :85908-96-9 MDL No. :MFCD02179046
Formula : C10H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :ULMHMJAEGZPQRY-UHFFFAOYSA-N
M.W : 199.25 Pubchem ID :7577838
Synonyms :

Calculated chemistry of [ 85908-96-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.79
TPSA : 46.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 1.31
Log Po/w (WLOGP) : 1.55
Log Po/w (MLOGP) : 1.16
Log Po/w (SILICOS-IT) : 1.14
Consensus Log Po/w : 1.46

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.7
Solubility : 3.95 mg/ml ; 0.0198 mol/l
Class : Very soluble
Log S (Ali) : -1.89
Solubility : 2.57 mg/ml ; 0.0129 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.4
Solubility : 7.97 mg/ml ; 0.04 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 85908-96-9 ]

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

Application In Synthesis of [ 85908-96-9 ]

* 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 [ 85908-96-9 ]
  • Downstream synthetic route of [ 85908-96-9 ]

[ 85908-96-9 ] Synthesis Path-Upstream   1~21

  • 1
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  • [ 98303-20-9 ]
Reference: [1] Organic letters, 2000, vol. 2, # 2, p. 155 - 158
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  • [ 20069-09-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593
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  • [ 85908-96-9 ]
  • [ 6052-73-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593
  • 4
  • [ 85908-96-9 ]
  • [ 27219-07-4 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 14, p. 2424 - 2426
  • 5
  • [ 85908-96-9 ]
  • [ 75178-90-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 7, p. 1324 - 1327
[2] Chemistry - An Asian Journal, 2018, vol. 13, # 17, p. 2559 - 2565
  • 6
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  • [ 75844-69-8 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 6, p. 1233 - 1239
  • 7
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  • [ 125541-22-2 ]
Reference: [1] Patent: US5936089, 1999, A,
  • 8
  • [ 675-20-7 ]
  • [ 24424-99-5 ]
  • [ 85908-96-9 ]
YieldReaction ConditionsOperation in experiment
91% With dmap; triethylamine In dichloromethane at 20℃; for 3 h; 395] To a solution of piperidin-2-one (0.97 g, 9.78 mmol) in DCM (20 mL) were added Et3N (1.36 mL, 9.78 mmol), DMAP (0.12 g, 0.978 mmol) and B0C2O (3.20 g, 14.7 mmol). The reaction mixture was stirred at room temperature for 3 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/7) to give the title compound as pale yellow oil (1.78 g, 91percent). MS (ESI, pos. ion) m z: 144.2 [(M-C4)+H]+; 1H MR (600 MHz, CDCI3): δ (ppm) 3.65 (t, J= 6.1 Hz, 2H), 2.50 (t, J = 9.6, 7.2 Hz, 2H), 1.82 (m, 4H), 1.52 (s, 9H).
91% With dmap; triethylamine In dichloromethane at 20℃; for 3 h; Step 1) fert-butyl 2-oxopiperidine-l-carboxylate [0359] To a solution of piperidin-2-one (0.97 g, 9.78 mmol) in DCM (20 mL) were added Et3N (1.36 mL, 9.78 mmol), DMAP (0.12 g, 0.978 mmol) and B0C2O (3.20 g, 14.7 mmol). The reaction mixture was stirred at rt for 3 h and then concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/7) to give the title compound as pale yellow oil (1.78 g, 91percent). MS (ESI, pos. ion) m/z: 144.2 [(M-C4)+H]+; NMR (600 MHz, CDCb): δ (ppm) 3.65 (t, J= 6.1 Hz, 2H), 2.50 (t, J= 9.6, 7.2 Hz, 2H), 1.82 (m, 4H), 1.52 (s, 9H).
91% With dmap; triethylamine In dichloromethane at 20℃; for 3 h; Piperidin-2-one (0.97 g, 9.78 mmol) was dissolved in DCM (20 mL) and then Et3N (1.36 mL, 9.78 mmol), DMAP (0.12 g, 0.978 mmol) and Boc2O (3.20 g, 14.7 mmol) were sequentially added to the solution to obtain a reaction system. The resulting reaction mixture was stirred at room temperature for 3 hours, then concentrated under reduced pressure and the resulting residue was subjected to silica gel column chromatography (EtOAc / PE (v / v) = 1/7) to give the title compound as a pale yellow oil (1.78 g, 91percent).
91% With dmap; triethylamine In dichloromethane at 20℃; for 3 h; Piperidin-2-one (0.97 g, 9.78 mmol) was dissolved in DCM (20 mL), and triethylamine (1.36 mL, 9.78 mmol), DMAP (0.12 g, 0.978 mmol) and Boc2O (3.20 g, 14.7 mmol) were added thereto and the resulting reaction mixture was stirred at room temperature for 3 hours and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (EtOAc / PE (v / v) = 1/7) to give a pale yellow oil (1.78 g, 91percent).
85% With dmap; triethylamine In dichloromethane at 0 - 20℃; for 48 h; To a stirred solution of piperidin-2-one (5 g, 50.4 mmol, 1.0 equiv.), triethylamine (14.022 mL, 100.9 mmol, 2.0 equiv.) and N,N-4-dimethylaminopyridine (0.123 g, 1.0 mmol) in methylene chloride (100 mL) at 0° C. was added di-tert-butyl dicarbonate (16.512 g, 75.7 mmol, 1.5 equiv.). The mixture was slowly warmed to room temperature and stirred for 48 hrs. The reaction was quenched with water and the organic layer was washed sequentially with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column (0-100percent ethyl acetate/hexanes) to afford the desired product as a yellow oil (8.5 g, 85percent). 1H NMR (300 MHz, CDCl3): δ 3.72-3.62 (m, 2H), 2.58-2.48 (m, 2H), 1.90-1.78 (m, 4H), 1.55 (s, 9H).
85% With dmap; triethylamine In dichloromethane at 0 - 20℃; for 48 h; To a stirred solution ofpiperidin-2-one (5 g, 50.4 mmol, 1.0 equiv.),triethylamine (14.022 mL, 100.9 mmol, 2.0 equiv.)andN,N-4-dimethylaminopyridine (0.123 g, 1.0 mmol)in dichloromethane (100 mL)at 0 °Cwas addeddi-tert-butyl dicarbonate (16.512 g, 75.7 mmol, 1.5 equiv.).The mixture was slowly warmed to room temperature and stirred for 48 hrs. The reaction was quenched with water and the organic layer was washed sequentially with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonateand saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate, filtered and concentratedin vacuo. The residue was purified by silica gel column (0-100percent ethyl acetate/hexanes) to afford the desired product as a yellow oil (8.5 g, 85percent).1H NMR (300 MHz, CDCl3): δ 3.72-3.62 (m, 2H), 2.58-2.48 (m, 2H), 1.90-1.78 (m, 4H), 1.55 (s, 9H).
82% With dmap In acetonitrile at 22℃; for 2 h; In addition, this reaction can also be performed in a different reaction step. In a three necked round bottom flask fitted with: a stirring bar, a thermometer, and a bubler at 22° C., 1000 mg, (10 mmol) ö-Valerolactam was placed. Then a 0.7M solution of DMAP (60 g 0.4 mmol) in ACN (0.8 mE) was added. To the light-yellow solution (BOC)20 (3260 g 15 mmol) was portion wise added accompanied by gas evolution. After flall conversion (stirring at internal temperature 22° C. for 2 h) 10 mE 0.1M HC1 aq. solution were added and extracted with dichloromethane (3x20 mE). The organic phase was evaporated. Upon addition of 40 ml hexane and cooling to —30° C. and crystals where formed. Yield 82percent. Purity 98percent. The advantage of this reaction compared to the reaction mentioned above can be seen in that the reaction is performed at room temperature and that DMAP is easier to handle compared to BuEi. Furthermore,a higher degree of purity is achievable.
77% With dmap; triethylamine In acetonitrile at 0 - 20℃; for 18 h; To a solution of 5.00 g (50.4 mmol, 1.0 eq.) 2-piperidinone in 250 mL acetonitrile, 8.44 mL (6.12 g,60.5 mmol, 1.2 eq.) triethylamine and 616 mg (5.04 mmol, 0.1 eq.) DMAP are added and the mixture iscooled to 0 °C. After slow addition of 12.7 mL (12.1 g, 55.4 mmol, 1.1 eq.) di-tert-butyl dicarbonate,the reaction mixture is stirred for 18 hours at ambient temperature. The solvent is removed and the crudeproduct is purified via column chromatography (SiO2, 6.5 10 cm, pentane/EtOAc = 5/1 3/1 1/1)to obtain 7.71 g (77 percent) tert-butyl-2-oxopiperidine-1-carboxylate as yellow oil.
67.25% With dmap; triethylamine In acetonitrile at 18℃; for 16 h; Inert atmosphere 10300] To a solution of compound 1 (31.00 g, 312.72 mmol) in CH3CN (500 mE) was added TEA (63.29 g, 625.44 mmol), 13oc20 (88.73 g, 406.54 mmol), DMAP (1.91 g, 15.64 mmol) in portions under N2. The mixture was stirred at 18° C. for 16 hours. TLC showed the reaction was completed. The mixture was concentrated in reduced pressure at 35° C. The residue was purified by silica gel chromatography (PE/EA30/1 to 5/1) to afford compound 2 (41.90 g, 210.29 mmol, 67.25percent yield) as yellow oil. LCMS:200 [M+1].
6.07 g With dmap In acetonitrile at 0℃; for 24 h; In 250mL eggplant-shaped flask were successively added piperidin-2-one (5g, 50mmol), di- tert -butyl dicarbonate (13.1g, 60mmol), acetonitrile, 100mL, ice-cooling to 0 , was slowly added portionwise 4- dimethylaminopyridine (1.22g, 10mmol, plus complete,The reaction temperature 24h, TLC the reaction was complete, solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1), to giveColorless oily liquid (6.07g, 30.5mmol).

Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 23, p. 7449 - 7458
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593
[3] Heterocycles, 2009, vol. 77, # 1, p. 417 - 432
[4] Patent: WO2015/94803, 2015, A1, . Location in patent: Paragraph 395
[5] Patent: WO2016/190847, 2016, A1, . Location in patent: Paragraph 0359
[6] Patent: CN104974163, 2017, B, . Location in patent: Paragraph 0583; 0584; 0585; 0586
[7] Patent: CN104672250, 2017, B, . Location in patent: Paragraph 0740; 0741; 0742; 0743
[8] Organic Letters, 2003, vol. 5, # 22, p. 4227 - 4230
[9] Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 6, p. 1233 - 1239
[10] Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 6, p. 1233 - 1239
[11] Organic and Biomolecular Chemistry, 2008, vol. 6, # 21, p. 4053 - 4058
[12] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 8, p. 1815 - 1823
[13] Tetrahedron Letters, 1989, vol. 30, # 32, p. 4309 - 4312
[14] Patent: US2015/284362, 2015, A1, . Location in patent: Paragraph 0281
[15] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 3, p. 293 - 297
[16] Journal of Organic Chemistry, 1983, vol. 48, # 14, p. 2424 - 2426
[17] Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10872 - 10874
[18] Patent: US2018/273477, 2018, A1, . Location in patent: Paragraph 0031; 0033; 0034
[19] New Journal of Chemistry, 2003, vol. 27, # 3, p. 475 - 482
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[23] Organic letters, 2000, vol. 2, # 2, p. 155 - 158
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YieldReaction ConditionsOperation in experiment
93% With potassium hydrogensulfate; N-ethyl-N,N-diisopropylamine In methanol 4-Benzensulfonylmethyl-4-hydroxy-piperidine TFA (B-1)
Diisopropylethylamine (28.3 mL, 162.75 mmol) and di-t-butyl dicarbonate (28.4 g, 130.02 mmol) were added in sequence to a mixture of piperidone hydrate hydrochloride (12) (10.0 g, 65.1 mmol) in methanol (50 mL).
The mixture was stirred at room temperature for 20 hours.
The solvent was removed, and the remaining was partitioned in ether and 1 M KHSO4 solution.
The organic layer was washed with brine and saturated NaHCO3.
The n-BuLi product was purified by flash chromatography to give a white solid (13) (12.0 g, 93percent).
Reference: [1] Patent: US6040316, 2000, A,
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Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 8, p. 2610 - 2618
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Reference: [1] RSC Advances, 2013, vol. 3, # 43, p. 19765 - 19768
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Reference: [1] Organic Letters, 2010, vol. 12, # 24, p. 5708 - 5711
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Reference: [1] Organic Letters, 2010, vol. 12, # 24, p. 5708 - 5711
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Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 49, p. 8949 - 8952
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Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 49, p. 8949 - 8952
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Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 49, p. 8949 - 8952
  • 17
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 11, p. 2631 - 2635
  • 18
  • [ 74-88-4 ]
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  • [ 677341-21-8 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 41, p. 7007 - 7009
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YieldReaction ConditionsOperation in experiment
38%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 0.25 h;
Stage #2: With mukaiyama’s reagent In tetrahydrofuran for 0.5 h;
Diisopropylamine (1.7 mL, 12.1 mmol) of THF (10 mL)To the solution was added n-butyllithium (6.7 ml, 11.0 mmol) was added dropwise at -78 ° C., and the mixture was stirred for 30 minutes. Compound 34 (2 g, 10.0 mmol) in THF (10 mL) was added dropwise, and the mixture was stirred for 15 minutes. A solution of N-tert-butylbenzenesulfinimidoyl chloride (2.6 g, 12.1 mmol) in THF (5 mL) was added and the mixture was stirred for 30 minutes. Water was added to the reaction solution, the mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane / ethyl acetate) to give Compound 35 (750 mg, yield: 38percent) as an orange solid.
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[5] Patent: WO2013/13188, 2013, A1,
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[7] Patent: US9416132, 2016, B2,
[8] Tetrahedron, 2017, vol. 73, # 27-28, p. 3866 - 3877
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  • [ 865245-32-5 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 18, p. 7324 - 7330
[2] Journal of Organic Chemistry, 2005, vol. 70, # 18, p. 7324 - 7330
[3] Patent: WO2017/223243, 2017, A1,
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Reference: [1] Patent: US2016/272599, 2016, A1,
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