Structure of 90481-32-6
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CAS No. : | 90481-32-6 |
Formula : | C4H9NO2 |
M.W : | 103.12 |
SMILES Code : | O[C@H]1CNC[C@@H]1O |
MDL No. : | MFCD08686737 |
InChI Key : | JCZPOYAMKJFOLA-IMJSIDKUSA-N |
Pubchem ID : | 146198 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 28.27 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.49 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.9 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-1.67 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-2.07 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.45 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.43 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.94 |
Log S (ESOL):? ESOL: Topological method implemented from |
0.57 |
Solubility | 386.0 mg/ml ; 3.74 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
1.08 |
Solubility | 1240.0 mg/ml ; 12.0 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
0.64 |
Solubility | 454.0 mg/ml ; 4.41 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
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 |
-8.11 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 |
2.0 |
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) |
1.76 |
* 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 |
---|---|---|
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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | 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℃; under 525.053 Torr; for 48h; | 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℃; under 525.053 Torr; for 48h; | 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 48h; | 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℃; under 5171.62 Torr; for 24h; | 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. |
With hydrogen;palladium on activated charcoal; In methanol; | (i) 3S,4S-Dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester Pd on C (300 mg) was added to a solution of (3S,4S)-(+)-benzyl-3,4-pyrrolidindiol (2.5 g, 12.9 mmol, commercially available) in MeOH. The reaction mixture was stirred under H2 balloon overnight, filtered thought Celite and concentrated under reduced pressure. The residue was dissolved in 1,4-dioxane (10 mL) and 6percent Na2CO3 was added to adjust pH ~10. Benzyl chloroformate (3.69 mL, 25.87 mmol) was added to the reaction mixture (during addition of benzyl chloroformate, 6percent Na2CO3 was added to adjust pH ~9). The reaction mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The residue was taken into water (50 mL) and extracted with EtOAc (2*50 mL). The organic layers were dried over MgSO4 and concentrated. The residue was purified by column chromatography (2percent CH3OH in CH2Cl2) to give colorless oil (1.51 g, 51percent). 1H NMR (300 MHz, CDCl3) delta7.28-7.34 (5H, m), 5.10 (1H, s), 4.12 (2H, m), 3.65-3.70 (2H, m), 3.36-3.43 (2H, m), 2.83 (1H, bs), 2.65 (1H, bs). | |
With hydrogen; acetic acid;10% palladium on charcoal; In methanol; under 2585.81 Torr; for 24h; | To a solution of SLnHK-01-3a (S,S) (5.0 g, 0.02 mol) in MeOH (35 mL) was added AcOH (15 mL) followed by addition of Pd/C (1.6 g). The mixture was then exposed to H2 at 50 psi for 24 h. The mixture was filtered through celite pad and filtrate was concentrated under reduced pressure to afford SLnHK-01-3 (S,S) (2.5 g, crude). The crude material was taken up for next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | General procedure: DIPEA (3 mol), HATU (1.5 mol) were added sequentially to a stirred solution of acid (1.1 mol) in DMF (10 v), after 5 minutes, corresponding amine (1.0 mol) was added, stirred at room temperature under argon atmosphere for 16 h. Then the reaction mixture was diluted with water (50 v), extracted with EtOAc (50 v X 2), evaporated the solvent in vacuo, the crude product was purified by column chromatography to afford 5/6(a-h), 5/6(m-s), 7(a-b), 10/11(a-c) and 10/11g (38-87%) as solids. |
Tags: 90481-32-6 synthesis path| 90481-32-6 SDS| 90481-32-6 COA| 90481-32-6 purity| 90481-32-6 application| 90481-32-6 NMR| 90481-32-6 COA| 90481-32-6 structure
A240395 [186393-21-5]
cis-Pyrrolidine-3,4-diol hydrochloride
Similarity: 0.96
A200586 [104706-47-0]
(R)-3-Hydroxypyrrolidine hydrochloride
Similarity: 0.92
A240395 [186393-21-5]
cis-Pyrrolidine-3,4-diol hydrochloride
Similarity: 0.96
A200586 [104706-47-0]
(R)-3-Hydroxypyrrolidine hydrochloride
Similarity: 0.92
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H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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The concentration of the dissolution solution you need to prepare is mg/mL