Structure of 498-63-5
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
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.
4.5
*For Research Use Only !
Change View
| Size | Price | VIP Price |
DE Stock US Stock |
Asia Stock Global Stock |
In Stock |
| {[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | {[ item.p_spot_brand_remark ]} 1-2 weeks {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.p_spot_brand_remark ]} 1-2 weeks {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock Inquiry - | Login - + |
Please Login or Create an Account to: See VIP prices and availability
Asia Stock: Ship in 3-5 business days
EU Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
{[ item.p_spot_brand_remark ]}
1-2weeks
Inquiry
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ item.p_spot_brand_remark ]}
1-2weeks
Inquiry
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
Asia Stock: Ship in 3-5 business days
EU Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
| CAS No. : | 498-63-5 |
| Formula : | C5H11NO |
| M.W : | 101.15 |
| SMILES Code : | OCC1CCCN1 |
| MDL No. : | MFCD00601073 |
| GHS Pictogram: |
|
| 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, |

[ 5337-03-1 ]
[ 498-63-5 ]
| 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. |

[ 498-63-5 ]
[ 101622-53-1 ]
[ 498-63-5 ]
[ 186692-41-1 ]
[ 498-63-5 ]
[ 1882-69-5 ]
[ 498-63-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| (RS)-2-Pyrrolidinemethanol Mass spectrum (m/z): 136 (M+) |
[ 4316-93-2 ]
[ 498-63-5 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 98% | In dichloromethane; at 20℃; for 16h; | Step 1. Synthesis of tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate A solution of 2-pyrrolidinemethanol (0.300 g, 1.98 mmol) in CH2Cl2 (5.0 mL) and di-tert-butyl dicarbonate (0.650 g, 1.98 mmol) were used to carry out the reaction. After the reaction was stirred at room temperature for 16 h and work-up, the residue was purified by Isco Combi-Flash Companion column chromatography (0-10percent MeOH in CH2Cl2) to give tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (0.590 g, 98percent). 1H NMR (CDCl3, 300 MHz) delta 4.78 (br d, 1H), 4.05-3.90 (br, 1H), 3.67-3.53 (m, 2H), 3.49-3.41 (m, 1H), 3.34-3.26 (m, 1H), 2.00 (dddd, 1H), 1.85-1.72 (m, 2H), 1.60-1.50 (m, 1H), 1.46 (s, 9H). |
| 90% | With triethylamine; In dichloromethane; at 20℃; | Step 1 Preparation of tert-butyl 2-(hydroxymethyl) pyrrolidine-1-carboxylate To a stirred mixture of pyrrolidin-2-ylmethanol (0.500 g, 4.95 mmol) and di-tert-butyl dicarbonate (2.16 g, 9.89 mmol) in DCM (10 mL) was added triethylamine (0.751 g, 7.42 mmol). The system was stirred at room temperature overnight. The reaction was quenched with water (10 mL) and extracted with EtOAc (20 mL*3). The combined organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (0.900 g, 90percent) as light yellow oil. |
| 48% | With triethylamine; In dichloromethane; at 20℃; for 3h; | To a solution of pyrrolidin-2-ylmethanol (505 mg, 4.99 mmol) and TEA (1.0 g, 9.9 mmol) in CH2Cl2 (5 mL) was added a solution of BoC2O (1.31 g, 6 mmol) in CH2Cl2 (10 mL). The reaction mixture was stirred for 3 h at room temperature. The reaction mixture was quenched with water (100 mL) and extracted with CH2Cl2, The organic layer was washed with brine, dried over Na2Spsi4, filtered, and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (MeOHiCH2Cl2 = 1: 100) to afford 14.2 g (48percent) of tert-butyl 2- (hydroxymethyl)pyrrolidine-l-carboxylate. LCMS ESI (+) m/z 202 (M+ 1) detected. |
| With potassium carbonate; In diethyl ether; water; at 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). | |
| Maleic acid (2.86g, 24.72 mmol) was added to pyrrolidin-2-ylmethanol(2.5g, 24.72 mmol) (A.170) in ethyl acetate (10 mL). The resultant mixture was stirred at room temperature for 2 hrs. After concentration, NaHCO3(10.38g, 123.6 mmol) in water (16 mL) was added to the residue. (BOC)2O (6.47 g, 29.66 mmol) was then added. The mixture was stirred at room temperature for 16 hrs. After removing solid by filtration, the aqueous solution was extracted with ethyl acetate. The organics were dried and concentrated, gave crude N-BOC protected pyrrolidin-2-ylmethanol. To the crude N-BOC protected pyrrolidin-2-ylmethanol(2.5g, 12.43mmol) and triethylamine (4.16ml, 29.82 mmol) in ethyl acetate at O0C, MsCl(1.16 mL, 14.91 mmol) was added and the mixture was stirred at 0°C for 2 hrs. The reaction was quenched with water and extracted with ethyl acetate. The organics were washed with 2N HCl, water, Sat. aq. NaHCO3, and brine, dried and concentrated. A portion of the residue(257.6 mg, 0.924mmol) was added to a mixture Of Cs2CO3 ( 301.1 mg, 0.924 mmol) and 4-(5-bromo-lH-indol-3-yl)-5-chloropyrimidin-2-amine A.170 (100 mg, 0.308 mmol) in DMF (1 mL) and DMSO(I mL). The mixture was heated at 110 0C for 16 hrs. After cooling to room temperature, the mixture was diluted with ether, washed with water and brine, dried and concentrated. A portion of the residue (68.5mg, 0.135 mmol) was dissolved in dichloromethane (8 mL) and TFA (2mL) then was added. The mixture was stirred at room temperature for 1 hr, concentrated and diluted with methanol-dichloromethane (1 :9). The solution was washed with Sat. aq. NaHCO3, and brine, dried and concentrated to afford 4-(5- bromo-l-(pyrrolidin-2-ylmethyl)-lH-indol-3-yl)-5-chloropyrimidin-2-amine (A.178) (32.0 mg, 58percent): 1H NMR (methanol- d4) b 8.78(s, 1 H), 8.43(s, 1 H), 8.15(s, 1 H), 7.42 (d, J= 8.0 Hz, 1 <n="98"/>H), 7.38(d, J= 8.0 Hz, 1 H), 4.29-4.15(m, 2 H), 3.55-3.45(m, 1 H), 3.00-2.95(m, 1 H), 2.90- 2.85(m, 1 H)), 1.92-1.80(m, 2 H), 1.80-1.72(m, 1 H), 1.55-1.46(m, 1 H); ms 406.0 (M+H+). |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 77.5% | With sodium carbonate; In chloroform; water; acetone; benzene; | (1) To a solution of 3.40 g (3.21 mmoles) of <strong>[498-63-5]2-hydroxymethylpyrrolidine</strong> [prepared in the manner described in J. O. C. 32, 2388 (1967) by P. G. Gassman and A. Fentiman] in a mixture of 20 ml of acetone and 4 ml of water are dropwise added 5.0 ml (1.34 equivalents) of benzoyl chloride and 10 ml of an aqueous solution of 4.5 g (1.34 equivalents) of sodium carbonate at the same time and after 30 minutes, water is added thereto. The mixture is extracted with methylene chloride. The organic layer is separated, washed with water, dried over sodium sulfate and evaporated under reduced pressure to yield 8.4 g of the residue, which is adsorbed on a column of 84 g of Kiesel Gel 60 (prepared by Merck Co.) and eluted with benzene, a mixture of benzene and chloroform, and chloroform, successively. The elude is evaporated under reduced pressure to yield 5.1 g of oily 1-benzoyl-<strong>[498-63-5]2-hydroxymethylpyrrolidine</strong> in 77.5percent yield. IR: numaxfilm 3400, 1615, 1607, 1575, 1500 cm-1. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; In tetrahydrofuran; at 20℃; for 10h; | The starting material of the intermediate 1 was dissolved in tetrahydrofuran, 4-dimethylaminopyridine was added, and benzyl chloroformate was added in portions, and the reaction was carried out for 10 hours at room temperature.The progress of the reaction was checked by TLC, the reaction was quenched, water and dichloromethane were extracted, and the organic phase was washed with acid and alkali, respectively.Concentration, separation and purification by column chromatography to obtain intermediate 2, |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium hydroxide; In water; acetone; | EXAMPLE 62 1-[(4-Methylphenyl)sulfonyl]-2-pyrrolidinemethanol To a stirred solution of 17 g (0.168 mole) of L-pyrrolidine-2-methanol in 100 ml of H2 O at 10° is added 32 g (0.168 mol) of p-toluenesulfonyl chloride in 100 ml of acetone over a 30 minute period. The pH of the solution is maintained at 11 by the addition of 2N NaOH solution. After stirring one hour more, the solution is evaporated in vacuo to one-half volume and acidified with conc. HCl. The solution is extracted with EtOAc, the EtOAc dried over MgSO4 and evaporated to an oil. The oil crystallized from ether-cyclohexane, 35 g (83percent), mp 90°-91°; [alpha]D23 -89.4° (c 1, methanol). Anal. Calcd for C12 H17 NO3 S: C, 56.44; H, 6.71; N, 5.49. Found: C, 56.51; H, 6.51; N, 5.41. |