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[ CAS No. 131878-23-4 ] {[proInfo.proName]}

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Chemical Structure| 131878-23-4
Chemical Structure| 131878-23-4
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Product Details of [ 131878-23-4 ]

CAS No. :131878-23-4 MDL No. :MFCD01321148
Formula : C16H24N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PHOIDJGLYWEUEK-CQSZACIVSA-N
M.W : 276.37 Pubchem ID :10286119
Synonyms :

Calculated chemistry of [ 131878-23-4 ]      Expand+

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.78

Safety of [ 131878-23-4 ]

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:

Application In Synthesis of [ 131878-23-4 ]

* 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.

  • Upstream synthesis route of [ 131878-23-4 ]
  • Downstream synthetic route of [ 131878-23-4 ]

[ 131878-23-4 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 131878-23-4 ]
  • [ 122536-77-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 721 - 739
  • 2
  • [ 131878-23-4 ]
  • [ 144043-17-4 ]
YieldReaction ConditionsOperation 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).
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1495 - 1510
[2] Patent: EP3327021, 2018, A1, . Location in patent: Paragraph 0086-0088
  • 3
  • [ 24424-99-5 ]
  • [ 114715-39-8 ]
  • [ 131878-23-4 ]
YieldReaction ConditionsOperation 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).
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1495 - 1510
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 721 - 739
  • 4
  • [ 100-52-7 ]
  • [ 122536-77-0 ]
  • [ 131878-23-4 ]
Reference: [1] Patent: WO2018/71343, 2018, A1, . Location in patent: Paragraph 1944
  • 5
  • [ 24424-99-5 ]
  • [ 131878-23-4 ]
YieldReaction ConditionsOperation 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).
Reference: [1] Patent: EP3327021, 2018, A1, . Location in patent: Paragraph 0083-0085
  • 6
  • [ 101385-90-4 ]
  • [ 131878-23-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826
  • 7
  • [ 116143-03-4 ]
  • [ 131878-23-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826
  • 8
  • [ 118354-71-5 ]
  • [ 131878-23-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826
  • 9
  • [ 130622-08-1 ]
  • [ 131878-23-4 ]
Reference: [1] Synthetic Communications, 1998, vol. 28, # 21, p. 3919 - 3926
  • 10
  • [ 397246-14-9 ]
  • [ 131878-23-4 ]
Reference: [1] Synthetic Communications, 1998, vol. 28, # 21, p. 3919 - 3926
  • 11
  • [ 100-46-9 ]
  • [ 322691-00-9 ]
  • [ 131878-23-4 ]
Reference: [1] Synthetic Communications, 1998, vol. 28, # 21, p. 3919 - 3926
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