Structure of 498-63-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 498-63-5 |
Formula : | C5H11NO |
M.W : | 101.15 |
SMILES Code : | OCC1CCCN1 |
MDL No. : | MFCD00601073 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335-H227 |
Precautionary Statements: | P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501 |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 31.91 |
TPSA ? Topological Polar Surface Area: Calculated from |
32.26 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.37 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.33 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.65 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.16 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.7 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.18 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.19 |
Solubility | 64.8 mg/ml ; 0.641 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.11 |
Solubility | 131.0 mg/ml ; 1.3 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.56 |
Solubility | 27.7 mg/ml ; 0.274 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.15 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.38 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 70℃;Inert atmosphere; | DL-Proline (6.0 g, 52.0 mmol) was added slowly and portion wise to a stirred suspension of LiAIH4 (3.0 g, 78.0 mmol) in THF (80 ml_) at 0 °C under nitrogen atmosphere carefully over a period of 30 minutes. The reaction mixture was warmed to room temperature and then heated to reflux for 3 h. The mixture was quenched with 20percent KOH solution at 0 °C slowly (18 - 20 mL). The mixture was filtered through a Celite? pad and washed ith THF. The filtered precipitate was again refluxed with THF for 30 minutes and filtered. The combined filtrates were concentrated to give K1 as pale yellow liquid which is slowly converts to dark brown liquid (3.2 g, 65percent). Rf: 0.1 (10percent MeOH in DCM & 1 drop AcOH, ninhydrin active). |
18% | To a solution of DL-proline (10Og, 869 mmol) in MeOH (1500 mL) was slowly added SOCl2 at 0 0C. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to give the crude material that was dissolved in THF (1700 mL) again. To this mixture was added portionwise LiAlH4 (132 g, 3.47 mol) at 0 0C. The resulting mixture was heated at 60 0C overnight. The excess LiAlH4 was quenched with KOH. The reaction mixture was filtered and the solid was washed with MeOH (1000 mL). The combined organic layers were dried, filtered, and concentrated under reduced pressure to give the crude material that was purified by distillation to afford 15.8 g (18percent) of pyrrolidin-2-ylmethanol. | |
With borane-THF; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 20℃; for 16h; | To a solution of DL-proline (10.0 g, 86.9 mmol) in THF (20 mL) were added boron trifluoride etherate complex (12.9 g, 91.2 mmol) and borane-tetrahydrofuran (1.0 mol/L THF solution, 100 mL) at 0°C, and the mixture was stirred at room temperature for 16 hr. After completion of the reaction, the mixture was further heated under reflux for 1 hr and cooled to room temperature. THF-water (1:1, 2.5 mL) and 6N sodium hydroxide were successively added to the reaction solution, and the mixture was heated under reflux for 2 hr. The reaction solution was cooled to room temperature, and concentrated under reduced pressure. The residue was washed with diethyl ether. The remaining residue, di-tert-butyl dicarbonate (19.9 g, 91.2 mmol) and potassium carbonate (36.0 g, 260 mmol) were dissolved in diethyl ether-water (100 mL-150 mL), and the mixture was stirred at room temperature for 16 hr. The diethyl ether layer was separated and washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5 - 60:40 - 50:50) to give the title compound (13.6 g, 76percent) as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 4.74 (d like, 1H), 3.96 (br s, 1H), 3.74-3.21 (m, 4H), 2.13-1.67 (m, 4H), 1.49 (s, 9H). |
With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 10h; | Using DL-proline as a starting material, dissolving in tetrahydrofuran, adding lithium aluminum hydride in portions, and reacting for 10 hours at room temperature.TLC detects the progress of the reaction, quenches the reaction, filters, concentrates, and recrystallizes the product to obtain intermediate 1, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With phosphoric acid; ruthenium-carbon composite; hydrogen; In water; at 150℃; under 60006.0 Torr; for 21h; | as a metal-supported catalyst, ruthenium carbon having a dispersity of 17.46percent, a metal surface area of 63.78 (m 2 / g), a particle diameter of 7.73 (nm), and a metal loading of 5percent A catalyst was prepared.In a pressure vessel, 100 g of water, 3.2 g of glutamic acid, 2.86 g of phosphoric acid and 0.16 g of ruthenium carbon catalyst were mixed. The mixture was stirred for 16 hours while pressurizing at 180 ° C. to a hydrogen pressure of 8 MPa. After completion of the reaction, the reaction mixture was filtered. When the components contained in the filtrate were analyzed by LC (liquid chromatography), prolinol was obtained in a yield of 35percent. Prolinol was synthesized under the same conditions as in Example 1. However, instead of glutamic acid, 2.8 g of pyroglutamic acid was used as a raw material. The reaction temperature was 150 ° C., and the reaction time was 21 hours. The yield of prolinol was 35percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(RS)-2-Pyrrolidinemethanol Mass spectrum (m/z): 136 (M+) |