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CAS No. : | 1194376-31-2 | MDL No. : | MFCD11878020 |
Formula : | C10H16N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BNJQQWIFMXEJPB-UHFFFAOYSA-N |
M.W : | 212.25 | Pubchem ID : | 45489887 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 57.54 |
TPSA : | 73.56 Ų |
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) : | -7.45 cm/s |
Log Po/w (iLOGP) : | 2.0 |
Log Po/w (XLOGP3) : | 0.2 |
Log Po/w (WLOGP) : | 0.5 |
Log Po/w (MLOGP) : | -0.07 |
Log Po/w (SILICOS-IT) : | 0.3 |
Consensus Log Po/w : | 0.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.08 |
Solubility : | 17.5 mg/ml ; 0.0824 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.3 |
Solubility : | 10.6 mg/ml ; 0.0497 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.73 |
Solubility : | 39.3 mg/ml ; 0.185 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.91 |
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: |
* 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 |
---|---|---|
52% | Stage #1: With sodium hydrogen sulfate In diethyl ether; water at 0℃; for 0.25 h; Stage #2: at 20℃; |
To a solution of 3-Oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (6 g, 32.4 mmol) in H2O/ether (85 mL/60 mL) was added sodium bisulphate (5.06 g, 48.6 mmol) at 0°C, stirred for 15 min and potassium cyanide (3.16 g, 48.6 mmol) was added and stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and washed with water 4 times. The orgnic layer was dried over anhydrous sodium sulphate and concentrated under vacuum. The residue was purified by flash column chromatography (DCM/MeOH::0-3percent) to provide the titled compound (52percent, 3.6 g). LCMS: 13.0(M+H), Rt. 3.2 min, 99.2percent (max). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32.6% | With potassium cyanide; 18-crown-6 ether In dichloromethane at 0 - 20℃; for 16 h; | Intermediate: tert-butyl 3-cyano-3-hydroxypyrrolidine-1-carboxylate To a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1 g, 5.40 mmol) in DCM (10 mL) was added trimethylsilyl cyanide (0.724 mL, 5.40 mmol), KCN (0.035 g, 0.540 mmol) and 18-CROWN-6 (0.143 g, 0.540 mmol) at 0° C. The reaction mixture was warmed to rt and stirred at rt for 16 h. The reaction mixture was cooled to 0° C., and quenched with sat. NaHCO3, then diluted with EtOAc. The organic phase was separated, washed with sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified on silica gel chromatography (0-100percent EtOAc/hex) to yield tert-butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate (0.5 g, 1.758 mmol, 32.6percent yield) and tert-butyl 3-cyano-3-hydroxypyrrolidine-1-carboxylate (0.306 g, 1.442 mmol, 26.7percent yield). tert-butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate: LC/MS (Cond. N-1): [M+H]+ 213.2, RT=4.359 min. 1H NMR (400 MHz, CHLOROFORM-d) 6 ppm 3.83-3.72 (m, 1H), 3.72-3.43 (m, 3H), 2.33 (q, J=6.8 Hz, 2H), 1.52-1.42 (m, 9H), 0.19-0.10 (m, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.21 g | With sodium hydrogencarbonate In diethyl ether; water at 0 - 20℃; for 24 h; | To a stirred solution of N-Boc-3-pyrrolidinone (CAS Number 101385-93-7; 4.0 g, 21.6 mmol) in diethyl ether (50 ml) and water (8 ml) was added NaHC03(3.6 g, 43 mmol) in water (5 ml) at 0°C. NaCN (3.17 g, 64.8 mmol) was added to the reaction mixture at 0°C. The reaction mixture was stirred at rt for 24 h. The resulting reaction mixture was poured into water (500 ml) and extracted with diethyl ether (2 x 300 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure yielding tert-butyl 3-cyano-3-hydroxypyrrolidine-l-carboxylate (4.21 g, 19.9 mmol). This material was used directly for the next step without further purification.1HNMR (400 MHz, DMSO-d6) δ ppm: 6.90 (s, 1 H), 3.48 - 3.63 (m, 2 H), 3.36 - 3.44 (m, 1 H), 3.20 - 3.32 (m, 1 H), 2.27 - 2.33 (m, 1 H), 2.13 - 2.20 (m, 1 H), 1.42 (s, 9 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32.6% | With potassium cyanide; 18-crown-6 ether In dichloromethane at 0 - 20℃; for 16 h; | Intermediate: tert-butyl 3-cyano-3-hydroxypyrrolidine-1-carboxylate To a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1 g, 5.40 mmol) in DCM (10 mL) was added trimethylsilyl cyanide (0.724 mL, 5.40 mmol), KCN (0.035 g, 0.540 mmol) and 18-CROWN-6 (0.143 g, 0.540 mmol) at 0° C. The reaction mixture was warmed to rt and stirred at rt for 16 h. The reaction mixture was cooled to 0° C., and quenched with sat. NaHCO3, then diluted with EtOAc. The organic phase was separated, washed with sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified on silica gel chromatography (0-100percent EtOAc/hex) to yield tert-butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate (0.5 g, 1.758 mmol, 32.6percent yield) and tert-butyl 3-cyano-3-hydroxypyrrolidine-1-carboxylate (0.306 g, 1.442 mmol, 26.7percent yield). tert-butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate: LC/MS (Cond. N-1): [M+H]+ 213.2, RT=4.359 min. 1H NMR (400 MHz, CHLOROFORM-d) 6 ppm 3.83-3.72 (m, 1H), 3.72-3.43 (m, 3H), 2.33 (q, J=6.8 Hz, 2H), 1.52-1.42 (m, 9H), 0.19-0.10 (m, 9H). |
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