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Chemical Structure| 90365-74-5
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Product Details of [ 90365-74-5 ]

CAS No. :90365-74-5 MDL No. :MFCD01073893
Formula : C11H15NO2 Boiling Point : -
Linear Structure Formula :(CH2CH(OH)CH(OH)CH2)NCH2C6H5 InChI Key :QJRIUWQPJVPYSO-QWRGUYRKSA-N
M.W : 193.24 Pubchem ID :2734057
Synonyms :

Calculated chemistry of [ 90365-74-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 57.66
TPSA : 43.7 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) : -7.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.73
Log Po/w (XLOGP3) : 0.3
Log Po/w (WLOGP) : -0.31
Log Po/w (MLOGP) : 0.58
Log Po/w (SILICOS-IT) : 0.83
Consensus Log Po/w : 0.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.41
Solubility : 7.48 mg/ml ; 0.0387 mol/l
Class : Very soluble
Log S (Ali) : -0.78
Solubility : 32.1 mg/ml ; 0.166 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.64
Solubility : 4.43 mg/ml ; 0.0229 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 90365-74-5 ]

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 [ 90365-74-5 ]

* 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 [ 90365-74-5 ]
  • Downstream synthetic route of [ 90365-74-5 ]

[ 90365-74-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 90365-74-5 ]
  • [ 90481-32-6 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With hydrogen; acetic acid In ethanol at 20℃; for 7 h;
Stage #2: With hydrogenchloride In 1,4-dioxane
To a solution of (3S,4S)-1-benzylpynolidne-3,4-diol (522 mg) in ethanol (15 mL) were added 10percent palladium-carbon (100 mg) and acetic acid (10 mL), and the mixture was reacted under pressurized hydrogen (40psi) at room temperature for 7 hours in Parr hydrogenation apparatus. The reaction solution was filtered through Celite, and the filtrate was concentrated under reduced pressure. To the resulting residue was added 4N hydrochloric acid-dioxane solution, and then the mixture was concentrated under reduced pressure to give the titled compound (373 mg) as a yellow solid (yield 99percent). MS(APCI)m/z; 104[M+H]+.
90.9% With palladium 10% on activated carbon; hydrogen In ethanol; water at 20℃; for 48 h; Intermediate ((3S, 4S) -5) (77.3g, 0.4mol) was dissolved in 80percent aqueous ethanol (2.4L) was added 10percent Pd / C (7.0g), at room temperature through hydrogen (0.07MPa) reaction 2d. The catalyst was removed by filtration and the filtrate concentrated under reduced pressure, the residue was treated with absolute ethanol (2 × 250mL) with traces of water addition to give a yellow oil of Intermediate ((3S, 4S) -6) 37.5g, yield 90.9percent.
90.9% With palladium 10% on activated carbon; hydrogen In ethanol; water at 20℃; for 48 h; Intermediate ((3S,4S)-5) (77.3 g, 0.4 mol) was dissolved in an aqueous solution of ethanol (80percent), to which10percent Pd/C (7.0 g) was added. Hydrogen (0.07 MPa) was supplied, and the reaction was kept for 2 days at room temperature.The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. Anhydrous ethanol(23250 mL) was used to remove the trace amount of water from the residue to obtain intermediate ((3S,4S)-6) as ayellow oil (37.5 g, yield: 90.9percent).MASS (ESI+) m/z = 104 (M+H)+.1 H NMR (400 MHz, DSO-d6): 2.60 (m, 2H), 3.02 (m, 2H), 3.83 (m, 2H), 4.81 (br s, 3H).
90.9% With palladium 10% on activated carbon; hydrogen In ethanol; water at 20℃; for 48 h; The intermediate ((3S, 4S)-5) (77.3 g, 0.4 mol) Soluble in 80percent aqueous ethanol solution (2.4L),Add 10percent Pd/C (7.0g),The reaction was carried out at room temperature with hydrogen (0.07 MPa) for 2 d.The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure.The residue was stripped of water with anhydrous ethanol (2×250 mL) to give a yellow oily intermediate ((3S, 4S)-6) 37.5 g, yield: 90.9percent.
83% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 24 h; General procedure: 10 percent Pd/C (1.50 g) was added to solution of 3a (7.50 g, 38.86 mmol) in ethanol (40 mL) under argon atmosphere, hydrogenated under 100 psi at room temperature for 24 h. The reaction mixture was filtered through celite pad, filtrate was evaporated in vacuo to get crude. The crude product was washed with n-pentane-diethyl ether mixture (1:1) (20 mL), decanted the organic layer and dried in vacuo yielding 3.28 g (82.0 percent) of light brown solid of compound 4a.

Reference: [1] Synthetic Communications, 2008, vol. 38, # 14, p. 2374 - 2384
[2] Patent: EP2390254, 2011, A1, . Location in patent: Page/Page column 86
[3] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 16, p. 2385 - 2390
[4] Angewandte Chemie, 1984, vol. 96, # 6, p. 425 - 426
[5] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 12, p. 3965 - 3973
[6] Tetrahedron, 2007, vol. 63, # 5, p. 1243 - 1253
[7] Journal of Carbohydrate Chemistry, 2000, vol. 19, # 4-5, p. 585 - 601
[8] Patent: CN105693520, 2016, A, . Location in patent: Paragraph 0154; 0155; 0156; 0157; 0158; 0159
[9] Patent: EP3067351, 2016, A1, . Location in patent: Paragraph 0073; 0074
[10] Patent: CN108658947, 2018, A, . Location in patent: Paragraph 0093; 0118; 0130-0132
[11] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2818 - 2823
[12] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1265 - 1268
[13] Synthesis, 2006, # 2, p. 247 - 256
[14] Patent: US2004/19065, 2004, A1, . Location in patent: Page/Page column 22
[15] Synthesis, 2010, # 5, p. 791 - 796
[16] Chemical Research in Toxicology, 2010, vol. 23, # 1, p. 118 - 133
[17] Patent: US2012/295874, 2012, A1, . Location in patent: Page/Page column 170
  • 2
  • [ 75172-31-5 ]
  • [ 90365-74-5 ]
YieldReaction ConditionsOperation in experiment
71% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 12 h; Inert atmosphere; Reflux Under nitrogen, cooled to LiAlH4 0 after (61.2g, 1.6mol) in tetrahydrofuran (3.6L) was slowly added a solution of Intermediate ((3R, 4R) -4) (132.7g, 0.6mol). The reaction mixture was refluxed for 12h, cooled to room temperature, ethyl acetate was added dropwise in an ice-water bath (144mL). Distilled water was added dropwise with vigorous stirring followed (61.2mL), 5percent NaOH (61.2mL) and distilled water (183.6mL). Filter cake was washed with hot tetrahydrofuran (2 × 1.2L) and washed. The combined filtrate and washings were concentrated under reduced pressure, the residue was separated and purified by silica gel column to give a pale yellow oil which was recrystallized from ethyl acetate as a white solid intermediate ((3S, 4S) -5) 82.3g, yield 71.0percent.
71% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 12 h; Inert atmosphere; Reflux Under a nitrogen atmosphere, intermediate ((3R,4R)-4) (132.7 g, 0.6 mol) was slowly added to a solution ofLiAlH4 (61.2 g, 1.6 mol) in tetrahydrofuran (3.6 L) which was cooled to 0°C. The reaction mixture was refluxed for 12 h,and cooled to room temperature. Ethyl acetate (144 mL) was added dropwise to the reaction mixture in a cold waterbath. Distilled water (61.2 mL), 5percent NaOH (61.2 mL) and distilled water (183.6 mL) were sequentially added dropwiseunder vigorous stirring. The mixture was filtered, and the filter cake was washed with hot tetrahydrofuran (231.2 L). Thefiltrate and wash solution were combined and concentrated under reduced pressure. The residue was separated on asilica gel column to obtain a light yellow oil, which was then recrystallized with ethyl acetate to obtain intermediate((3S,4S)-5) as a white solid (82.3 g, yield: 71.0percent).MASS (ESI+) m/z = 194 (M+H)+.1 H NMR (400 MHz, DSO-d6): 2.30 (dd, 2H), 2.74 (dd, 2H), 3.46 (d, 1H), 3.57 (d, 1H), 3.84 (m, 2H), 4.84 (br s, 2H),7.20-7.35 (m, 5H).
69% With lithium aluminium tetrahydride In tetrahydrofuran at -5 - 95℃; for 12 h; Lithium aluminum tetrahydrate (5 g, 132 mmol)Was dissolved in anhydrous tetrahydrofuran (100 ml)A solution of (3R, 4R) -1-benzyl-3,4-dihydroxy-2,5-pyrrolidinedione (10 g, 45 mmol) in dry tetrahydrofuran was added at -5 ° C. After completion of the dropwise addition, The reaction was allowed to proceed to 95 ° C for 12 hours,Cooled to room temperature, 6.8 g of water was added dropwise to the reaction system, and the floc was present. Then, 6.8 g of 20percent NaoH solution and 20.4 g of water were added. Filtered and purified under reduced pressure and purified by silica gel column chromatography (dichloromethane: methanol = 50: 1)To give 6 g of (3S, 4S) -1-benzyl-3,4-pyrrolidine diol (pale yellow solid in 69percent yield).
61%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -5 - 20℃; Heating / reflux
Stage #2: With ammonium chloride In water
The (3R,4R)-l-benzyl-3,4-dihydroxypyrrolidine-2,5-dione (0.98 g, 4.4 mmol) <n="124"/>in THF (20 ml) was added slowly to a stirring solution Of LiAlH4 (4.75 ml, 11.87 mmol of 2.5 M solution in THF) in THF cooled to -5°C. After complete addition, the reaction was warmed to room temperature, then heated at reflux overnight. The reaction was cooled to room temperature, then quenched with saturated aqueous NH4Cl until further addition produced no more bubbling. The reaction was diluted with ethyl acetate (20 ml), filtered, and the solid washed with ethyl acetate. The combined filtrates were concentrated, and the residue purified by silica flash chromatography (gradient elution, using EtOAc, and 9: 1 EtOAc-EtOH) to provide the title compound as a tan solid (0.52 g, 61percent).
45%
Stage #1: With sodium tetrahydroborate; boron trifluoride diethyl etherate In 1,2-dimethoxyethane at 0 - 70℃; for 2 h;
Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water at 70℃; for 0.25 h;
Stage #3: With sodium fluoride In 1,2-dimethoxyethane; water for 0.5 h; Reflux
To a stirred solution of boron trifluoride ethyl etherate (23 mL, 0.16 mol) in DME (120 mL) were added SLnHK-01-2a (10 g, 0.04 mol) and sodium borohydride (6.2 g, 0.16 mol) at 0° C. The mixture was stirred at 70° C. for 2 h. Then 6 N HCl (62.5 mL) was added slowly at 70° C., stirred for 15 min. Sodium fluoride (28 g) was added and the mixture was heated at reflux temperature for 30 min. The mixture was cooled to room temperature, 20percent aq. NaOH (53 mL) was added and the resulting mixture was filtered. The organic phase was isolated, evaporated to dryness and obtained residue was partitioned between water and diethyl ether. The water phase was extracted with diethyl ether (2x100 mL). The combined organic phases were dried over MgSO4, evaporated to dryness and obtained crude material was recrystallized from ethyl acetate to obtain SLnHK-01-3a (S,S) (7.0 g, 45percent) as white crystals.1H NMR (200 MHz, CDCl3): δ 7.34-7.25 (m, 5H), 4.04 (t, J=4.2 Hz, 2H), 3.58 (d, J=7.8 Hz, 2H), 2.92-2.88 (m, 2H), 2.44-2.40 (m, 2H).
12% With borane-THF In tetrahydrofuran at 20 - 60℃; for 2 h; To a mixture of (3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione (44 g, 199 mmol, 1.0 eq) and THF (176 mL) at 20° C. (vessel jacket temperature) was added borane-tetrahydrofuran complex (1.0 mol/L) in THF (800 mL, 800 mmol, 1.0 mol/L, 4.0 eq) at a rate to maintain the temperature between 20° C. and 25° C. Over 1 hr, the jacket temperature was ramped to 60° C. and then held for 1 hr. Upon completion, the reaction was cooled to 30° C. and quenched by the slow dropwise addition of MeOH (97 mL, 12 eq) to the mixture at a rate to control off gassing. The reaction mixture was then heated to reflux and concentrated to a low stir volume. The reaction solvent THF was then replaced by a constant volume displacement with MeOH (total of 1.5 L). Once the THF content had been reduced to less than 1 wt percent, MeOH was replaced by a constant volume displacement with EtOAc (total of 1.5 L) to reduce the MeOH content to less than 1 wt percent. The total volume of EtOAc was then readjusted to about 250 mL (6 vol) and then cooled to 5° C. to crystallize the product. The desired product was isolated by filtration, washed with cold EtOAc (88 mL) and dried to give title compound (27.0 g, 140 mmol, 70percent). A second crop of product was isolated by concentration of the combined filtrate and cake wash to half volume, which was then cooled to 5° C., filtered and washed with cold EtOAc (50 mL) to afford additional title compound (4.5 g, 23 mmol, 12percent). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.33-7.26 (m, 4H) 7.25-7.20 (m, 1H) 4.48 (d, J=4.8 Hz, 2H) 3.38-3.31 (m, 2H), 3.57 (d, J=13.0 Hz, 1H) 3.46 (d, J=13.0 Hz, 1H) 2.74 (dd, J=9.4, 5.9 Hz, 2H) 2.30 (dd, J=9.4, 4.4 Hz, 2H). m/z (EI+) for C11H15NO2 194.2 (M+H)+

Reference: [1] Tetrahedron, 2007, vol. 63, # 5, p. 1243 - 1253
[2] Angewandte Chemie, 1984, vol. 96, # 6, p. 425 - 426
[3] Patent: CN105693520, 2016, A, . Location in patent: Paragraph 0148; 0149; 0159; 0151; 0152; 0153
[4] Patent: EP3067351, 2016, A1, . Location in patent: Paragraph 0071; 0072
[5] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2219 - 2224
[6] Tetrahedron Asymmetry, 1997, vol. 8, # 11, p. 1861 - 1867
[7] Patent: CN106946744, 2017, A, . Location in patent: Paragraph 0083; 0186-0187
[8] Angewandte Chemie - International Edition, 1998, vol. 37, # 13-14, p. 1846 - 1850
[9] Journal of Organic Chemistry, 2000, vol. 65, # 6, p. 1750 - 1757
[10] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 957 - 971
[11] Synthesis, 2010, # 5, p. 791 - 796
[12] Patent: WO2008/24725, 2008, A1, . Location in patent: Page/Page column 122-123
[13] Synthetic Communications, 2008, vol. 38, # 14, p. 2374 - 2384
[14] Synlett, 2009, # 5, p. 747 - 750
[15] Patent: US2012/295874, 2012, A1, . Location in patent: Page/Page column 169; 170
[16] Patent: US2015/141402, 2015, A1, . Location in patent: Paragraph 0650; 0651
[17] Chemische Berichte, 1986, vol. 119, # 11, p. 3326 - 3343
[18] Heterocycles, 1992, vol. 34, # 8, p. 1519 - 1522
[19] Journal of Organic Chemistry, 1996, vol. 61, # 23, p. 8099 - 8102
[20] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 16, p. 2385 - 2390
[21] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1265 - 1268
[22] Patent: EP1577301, 2005, A1, . Location in patent: Page/Page column 162
[23] Patent: US5585500, 1996, A,
[24] Patent: US2005/20645, 2005, A1,
[25] Tetrahedron, 2008, vol. 64, # 7, p. 1197 - 1203
[26] Patent: EP1405852, 2004, A1, . Location in patent: Page 150
[27] Chemical Research in Toxicology, 2010, vol. 23, # 1, p. 118 - 133
[28] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1810 - 1814
  • 3
  • [ 187032-53-7 ]
  • [ 90365-74-5 ]
YieldReaction ConditionsOperation in experiment
86.59% With borane-THF In tetrahydrofuran at 70℃; for 3 h; General procedure: Borane in THF (1.0 M) (17.19 mL, 180.99 mmol) was added drop-wise to a solution of 2a (10.0 g, 45.24 mmol) in THF (200 mL) at RT, after completion of addition, reaction mixture was slowly heated to 70 °C for 3 h. The reaction mixture was cooled to 0 °C, quenched with methanol (50 mL) by the drop-wise addition, slowly warmed to RT, stirred for 1 h. (Note: intensive gas evolution is occurred). The reaction mixture was concentrated in vacuo, crude was purified on a silica gel column using a linear gradient of ethyl acetate in Pet-ether yielding 7.73 g (88.5percent) of yellowish crystals of compound 3a.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2818 - 2823
  • 4
  • [ 1031246-25-9 ]
  • [ 90365-74-5 ]
Reference: [1] Synthetic Communications, 2008, vol. 38, # 9, p. 1365 - 1374
  • 5
  • [ 87-69-4 ]
  • [ 100-46-9 ]
  • [ 90365-74-5 ]
Reference: [1] Patent: US6090950, 2000, A,
[2] Collection of Czechoslovak Chemical Communications, 2012, vol. 77, # 3, p. 224 - 233
  • 6
  • [ 100-46-9 ]
  • [ 90365-74-5 ]
Reference: [1] Chemical Research in Toxicology, 2010, vol. 23, # 1, p. 118 - 133
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1810 - 1814
[3] Patent: US2012/295874, 2012, A1,
[4] Patent: US2015/141402, 2015, A1,
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 957 - 971
[6] Patent: EP3067351, 2016, A1,
[7] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2818 - 2823
[8] Patent: CN106946744, 2017, A,
  • 7
  • [ 57495-46-2 ]
  • [ 100-46-9 ]
  • [ 90365-74-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 3, p. 823 - 826
  • 8
  • [ 136137-85-4 ]
  • [ 90365-74-5 ]
Reference: [1] Arkivoc, 2010, vol. 2010, # 5, p. 64 - 69
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