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[ CAS No. 915226-43-6 ] {[proInfo.proName]}

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Chemical Structure| 915226-43-6
Chemical Structure| 915226-43-6
Structure of 915226-43-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 915226-43-6 ]

CAS No. :915226-43-6 MDL No. :MFCD11977492
Formula : C11H20N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :APFUDGDIIFSTSD-MRVPVSSYSA-N
M.W : 228.29 Pubchem ID :26343680
Synonyms :

Calculated chemistry of [ 915226-43-6 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.82
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 64.31
TPSA : 72.63 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) : -7.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 0.48
Log Po/w (WLOGP) : 0.74
Log Po/w (MLOGP) : 0.62
Log Po/w (SILICOS-IT) : 0.26
Consensus Log Po/w : 0.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.29
Solubility : 11.6 mg/ml ; 0.0508 mol/l
Class : Very soluble
Log S (Ali) : -1.57
Solubility : 6.08 mg/ml ; 0.0266 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.87
Solubility : 30.7 mg/ml ; 0.135 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.74

Safety of [ 915226-43-6 ]

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 [ 915226-43-6 ]

* 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 [ 915226-43-6 ]
  • Downstream synthetic route of [ 915226-43-6 ]

[ 915226-43-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 915226-43-6 ]
  • [ 188111-79-7 ]
YieldReaction ConditionsOperation in experiment
80% With sodium hypochlorite; sodium hydroxide In water at 15 - 25℃; for 16 h; Example 28 Method for producing (R)-1-(tert-butoxycarbonyl)-3-aminopiperidine To a solution (amount 9 g) of (R)-1-(tert-butoxy carbonyl)nipecotamide (net weigh of (R)-1-(tert-butoxycarbonyl) nipecotamide: 0.7 g), Sodium hydroxide (1.3 g, 10 equivalents) and an aqueous sodium hypochlorite solution (2.2 g, 1.1 equivalents) were added. The mixture was stirred at 15 to 25° C. for 16 hours. The water layer was removed, and the solvent was evaporated under reduced pressure. Toluene (10 ml) and saturated brine (5 ml) were added thereto, and the water layer was removed. The solvent was evaporated under reduced pressure to obtain the title compound as yellow oil (0.7 g, net weight: 0.5 g, yield: 80percent).
Reference: [1] Patent: US2010/105917, 2010, A1, . Location in patent: Page/Page column 21
  • 2
  • [ 4138-26-5 ]
  • [ 24424-99-5 ]
  • [ 915226-43-6 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: at 30℃; for 60 h; Aqueous phosphate buffer; Enzymatic reaction
Stage #2: With sodium hydroxide In tetrahydrofuran at 20℃; for 1 h;
Example 5Method for producing (R)-1-(tert-butoxycarbonyl)nipecotamide To the reaction mixture obtained in Example 4, THF (40 ml) was added, and di-tert-butyl dicarbonate (37.2 g, 2.3 equivalents) was added thereto. The pH of the reaction mixture was adjusted to 10.0 using NaOH. The reaction mixture was stirred for 1 hour at room temperature, and then the precipitated crystal was filtered off to obtain (R)-1-(tert-butoxycarbonyl)nipecotamide as white crystal (15.6 g, yield: 93percent). The crystal was analyzed by the method of Example 3; as a result, the optical purity was 99.8percent ee.1H NMR (400 MHz, CDCl3): δ5.36 (brs, 2H), 3.94-3.08 (m, 5H), 1.96-1.36 (m, 13H)
Reference: [1] Patent: US2010/105917, 2010, A1, . Location in patent: Page/Page column 16
  • 3
  • [ 163438-09-3 ]
  • [ 915226-43-6 ]
Reference: [1] Patent: US2007/276002, 2007, A1, . Location in patent: Page/Page column 15
  • 4
  • [ 915226-43-6 ]
  • [ 915226-44-7 ]
YieldReaction ConditionsOperation in experiment
100% at 0 - 20℃; 2(B)
(R)-3-Cyano-piperidine-1-carboxylic acid tert-butyl ester
Phosphorus oxychloride (203 μL, 2.18 mmol) was added dropwise at 0° C. to a solution of (R)-3-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 2.18 mmol) in pyridine (10 mL), under nitrogen atmosphere.
After stirring overnight at room temperature, ethyl acetate was added and the solution was washed with 10percent HCl (2 times).
The phases were separated and the organics were dried over sodium sulphate and evaporated to dryness under reduced pressure.
The title compound was used for the next step without further purification.
Yield: quantitative; LCMS (T): 4.48 min (Method A); MS (ES+) gave m/z: 211.1.
Reference: [1] Patent: US2009/215822, 2009, A1, . Location in patent: Page/Page column 10
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