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CAS No. : | 131878-23-4 | MDL No. : | MFCD01321148 |
Formula : | C16H24N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PHOIDJGLYWEUEK-CQSZACIVSA-N |
M.W : | 276.37 g/mol | Pubchem ID : | 10286119 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.56 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 83.88 |
TPSA : | 41.57 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.1 cm/s |
Log Po/w (iLOGP) : | 3.23 |
Log Po/w (XLOGP3) : | 2.66 |
Log Po/w (WLOGP) : | 2.25 |
Log Po/w (MLOGP) : | 2.18 |
Log Po/w (SILICOS-IT) : | 2.12 |
Consensus Log Po/w : | 2.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.06 |
Solubility : | 0.243 mg/ml ; 0.00088 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.18 |
Solubility : | 0.181 mg/ml ; 0.000654 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.97 |
Solubility : | 0.0298 mg/ml ; 0.000108 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.78 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
98.6% | With lithium aluminium tetrahydride In tetrahydrofuran at -40℃; for 4 h; Reflux | A tert-butyl (R)-(1-benzylpyrrolidin-3-yl)carbamate 2aa (3.20g, 11.6mmol) solution in 58.0mL of 61 tetrahydrofuran was placed in a 100mL round-bottom flask. After it was cooled at −40°C, 62 lithium aluminum hydride (2.64g, 69.6mmol) was slowly added to the stirred mixture. The reaction mixture was refluxed for 4h and then cooled down to −40°C. The reaction was quenched with 2.70mL of deionized 46 water, 2.70mL of 15percent 63 sodium hydroxide solution, and 8.10mL of deionized water. Then, Celite 545 was added and the mixture was stirred for 30min before being filtered through a Celite 545 pad. The filtered solution was concentrated under reduced pressure and the residue was extracted with dichloromethane three times. Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with flash column chromatography (methanol: dichloromethane: ammonium hydroxide=5:90:5). Removing the solvent in vacuo provided 2.17g of 64 (R)-1-benzyl-N-methylpyrrolidin-3-amine (98.6percent yield). 1H NMR (400MHz, CDCl3) δ 7.34–7.24 (m, 5H), 3.62 (s, 2H), 3.25–3.19 (m, 1H), 2.74 (dd, J=9.4, 6.8Hz, 1H), 2.64 (dt, J=8.6, 6.0Hz, 1H), 2.52 (dt, J=8.4, 6.0Hz, 1H), 2.41–2.37 (m, 1H), 2.38 (s, 3H), 2.19–2.09 (m, 1H), 2.02 (bs, 1H), 1.63–1.56 (m, 1H). |
0.98% | With lithium aluminium tetrahydride In tetrahydrofuranReflux | After 3.204 g of tert-butyl (R)-(1-benzylpyrrolidine-3-yl)carbamate was added to a 100-mL round-bottomed flask, 58.0 mL of tetrahydrofuran and 2.639 g of lithium aluminum hydride (LiAlH4) were sequentially added thereto. The reaction mixture was refluxed overnight and then cooled at 0°C. 2.7 mL of deionized water was slowly added to the reaction mixture while cooling. After the reaction mixture was stirred for about 5 minutes, 2.7 mL of a 15percent sodium hydroxide (NaOH) aqueous solution was added thereto. The reaction mixture was further stirred for about 5 minutes, and then 8.1 mL of deionized water was added thereto to terminate the reaction. The reaction mixture was filtered through a Celite™ 545 filter agent (available from DAEJUNG Chemicals & Metals Co., Ltd.).The resulting filtrate was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (MeOH:CH2Cl2:NH4OH=5:90:5). As a result, 2.174 g of (R)-1-benzyl-N-methylpyrrolidine-3-amine was obtained with a yield of about 98.6percent. (0088) 1H NMR (400 MHz, CDCl3) δ7.34-7.24 (m, 5H), 3.62 (s, 2H), 3.25-3.19 (m, 1H), 2.74 (dd, J = 9.4, 6.8 Hz, 1H), 2.64 (dt, J = 8.6, 6.0 Hz, 1H), 2.52 (dt, J = 8.4, 6.0 Hz, 1H), 2.41-2.37 (m, 1H), 2.38 (s, 3H), 2.19-2.09 (m, 1H), 2.02 (bs, 1H), 1.63-1.56 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.2% | Stage #1: With sodium hydrogencarbonate In water; acetonitrile at 20℃; for 0.166667 h; Stage #2: at 20℃; |
Sodium bicarbonate (5.92 g, 70.5 mmol) in 118 mL of deionized water was added to (3R)-(+)-benzylaminopyrrolidine 1a (5.00 g, 28.4 mmol) solution in 118 mL of acetonitrile and the mixture was stirred at room temperature for 10 min. Di-tert-butyl dicarbonate (6.22 g, 28.5 mmol) was then added and the mixture was stirred at room temperature overnight. After the reaction, the solution was concentrated under reduced pressure and the residue was extracted with dichloromethane three times. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with flash column chromatography (methanol: dichloromethane = 2:98). Removing the solvent in vacuo provided 4.24 g of tert-butyl (R)-(1-benzylpyrrolidin-3-yl)carbamate (65.2percent yield). 1H NMR (400 MHz, CDCl3) δ 7.36-7.26 (m, 5H), 4.86 (bs, 1H), 4.18 (bs, 1H), 3.61 (s, 2H), 2.79 (bs, 1H), 2.65-2.61 (m, 1H), 2.54 (d, J = 8.0 Hz, 1H), 2.34-2.25 (m, 2H), 1.61-1.51 (m, 1H), 1.46 (s, 9H). [α]D +2.5° (c 0.620, CHCl3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.65% | With sodium hydrogencarbonate In water; acetonitrile | 5.000 g of (3R)-(-)-1-benzyl-3-aminopyrrolidine hydrochloride (available from Hangzhou Tacon Co., Ltd.) was added to a 500-mL round-bottomed flask, and 117.5 mL of deionized water and 117.5 mL of acetonitrile were sequentially added thereto. After 5.924 g of sodium hydrogen carbonate (NaHCO3) and 6.218 g of di-tert-butyl dicarbamate (BoC2O) were sequentially added thereto, the reaction mixture was vigorously stirred overnight. An organic phase was separated from the reaction mixture, and then the resulting aqueous phase was extracted twice with 50 mL of dichloromethane (CH2Cl2). The collected organic phase was distilled under reduced pressure. The resulting residue was purified by flash column chromatography (MeOH:CH2Cl2=2:98). As a result, 4.235 g of tert-butyl (R)-(1-benzylpyrrolidine-3-yl)carbamate was obtained with a yield of about 65.2percent. 1H NMR (400 MHz, CDCl3) δ 7.36-7.26 (m, 5H), 4.86 (bs, 1H), 4.18 (bs, 1H), 3.61 (s, 2H), 2.79 (bs, 1H), 2.65-2.61 (m, 1H), 2.54 (d, J = 8.0 Hz, 1H), 2.34-2.25 (m, 2H), 1.61-1.51 (m, 1H), 1.46 (s, 9H). |
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