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[ CAS No. 137496-71-0 ] {[proInfo.proName]}

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Chemical Structure| 137496-71-0
Chemical Structure| 137496-71-0
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Product Details of [ 137496-71-0 ]

CAS No. :137496-71-0 MDL No. :MFCD06858469
Formula : C10H19NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PPUYUEPZGGATCN-QMMMGPOBSA-N
M.W : 185.26 Pubchem ID :9794078
Synonyms :

Calculated chemistry of [ 137496-71-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.59
TPSA : 29.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.76
Log Po/w (XLOGP3) : 2.03
Log Po/w (WLOGP) : 2.02
Log Po/w (MLOGP) : 1.71
Log Po/w (SILICOS-IT) : 1.23
Consensus Log Po/w : 1.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.07
Solubility : 1.58 mg/ml ; 0.00852 mol/l
Class : Soluble
Log S (Ali) : -2.28
Solubility : 0.977 mg/ml ; 0.00527 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.38
Solubility : 7.69 mg/ml ; 0.0415 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.38

Safety of [ 137496-71-0 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P261-P273-P280-P301+P310-P305+P351+P338 UN#:2922
Hazard Statements:H227-H301-H315-H318-H335-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 137496-71-0 ]

* 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 [ 137496-71-0 ]
  • Downstream synthetic route of [ 137496-71-0 ]

[ 137496-71-0 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 132482-10-1 ]
  • [ 137496-71-0 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With lithium triethylborohydride In tetrahydrofuran at 0 - 20℃;
Stage #2: With water In tetrahydrofuran; ethyl acetate
Slowly add lithium triethylborohydride (1M in THF, 17 mL, 17. mmol) to a 0 °C solution of 2R-methanesulfonyloxymethyl-pyrrolidine-l-carboxylic acid tert-butyl ester (1.6 g, 5.73 mmol) in 10 mL of tetrahydrofuran. Warm the reaction mixture to ambient temperature and stir for 16 hours. Dilute the reaction mixture with ethyl acetate and water and wash successively with 0.1N HC1 and brine. Dry the crude organic extracts over MgS04, filter and concentrate to afford the title compound as a clear oil (0.930 g, 88percent). 400 MHz NMR (CDC13) 8 3.83 (m, 1H), 3.38 (m, 2H), 1.92 (m, 3H), 1.58 (m, 1H), 1.48 (s, 9H), and 1.2 (d, J = 8 Hz, 3H).
Reference: [1] Patent: WO2006/19833, 2006, A1, . Location in patent: Page/Page column 61
[2] Tetrahedron Letters, 1995, vol. 36, # 8, p. 1223 - 1226
  • 2
  • [ 128510-88-3 ]
  • [ 137496-71-0 ]
YieldReaction ConditionsOperation in experiment
79% With lithium triethylborohydride In tetrahydrofuran at 0℃; for 15 h; Step 3:
Preparation of 2-(S)-methyl-pyrrolidine-1-carboxylic Tert-butyl Ester (5)
To a solution of 2-(S)-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (compound (4), 1.77 g, 4.99 mmol) in 5 ML of THF at 0° C. was added dropwise 15 ML (15 mmol) of a 1 M THF solution of lithium triethylborohydride.After 15 hours, the reaction was quenched by addition of 7.39 ML of water.The reaction was diluted with 35 ML of chloroform, and poured into a separatory funnel.The mixture was diluted with dichloromethane and washed with saturated aqueous NaCl solution.The organic phase then was dried over sodium sulfate.The mixture was concentrated in vacuo and purified by flash chromatography on silica gel, eluding with 1:3 ethyl acetate/hexane to give pure product as a clear oil (0.73 g, 79percent yield).
79% With lithium triethylborohydride In tetrahydrofuran at 0℃; for 15 h; Step 3:
Preparation of 2-(S)-methyl-pyrrolidine-1-carboxylic tert-butyl ester (5)
To a solution of 2-(S)-(toluene-4-sulfonyloxymethyl)-pyrrolidine- 1-carboxylic acid tert-butyl ester (compound (4), 1.77 g, 4.99 mmol) in 5 mL of THF at 0° C. was added dropwise 15 mL (15 mmol) of a 1 M THF solution of lithium triethylborohydride.
After 15 hours, the reaction was quenched by addition of 7.39 mL of water.
The reaction was diluted with 35 mL of chloroform, and poured into a separatory funnel.
The mixture was diluted with dichloromethane and washed with saturated aqueous NaCl solution.
The organic phase then was dried over sodium sulfate.
The mixture was concentrated in vacuo and purified by flash chromatography on silica gel, eluding with 1:3 ethyl acetate/hexane to give pure product as a clear oil (0.73 g, 79percent yield).
Reference: [1] Patent: US2004/171845, 2004, A1, . Location in patent: Page 8
[2] Patent: US2004/260100, 2004, A1, . Location in patent: Page 8
  • 3
  • [ 86953-79-9 ]
  • [ 77-78-1 ]
  • [ 137496-71-0 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 2, p. 315 - 321
  • 4
  • [ 77-78-1 ]
  • [ 137496-71-0 ]
  • [ 157007-54-0 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 2, p. 315 - 321
  • 5
  • [ 24424-99-5 ]
  • [ 765-38-8 ]
  • [ 137496-71-0 ]
Reference: [1] Tetrahedron, 1994, vol. 50, # 20, p. 6089 - 6096
[2] Organic and Biomolecular Chemistry, 2010, vol. 8, # 20, p. 4533 - 4535
  • 6
  • [ 74-88-4 ]
  • [ 137496-71-0 ]
Reference: [1] Patent: WO2008/73825, 2008, A1, . Location in patent: Page/Page column 292-294
  • 7
  • [ 86953-79-9 ]
  • [ 77-78-1 ]
  • [ 137496-71-0 ]
  • [ 157007-54-0 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 21, p. 5424 - 5427
  • 8
  • [ 59378-81-3 ]
  • [ 137496-71-0 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 8, p. 1223 - 1226
  • 9
  • [ 37784-17-1 ]
  • [ 137496-71-0 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 8, p. 1223 - 1226
  • 10
  • [ 24424-99-5 ]
  • [ 137496-71-0 ]
  • [ 157007-54-0 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 21, p. 5424 - 5427
  • 11
  • [ 86953-79-9 ]
  • [ 74-88-4 ]
  • [ 137496-71-0 ]
  • [ 157007-54-0 ]
Reference: [1] Journal of the American Chemical Society, 1994, vol. 116, # 8, p. 3231 - 3239
  • 12
  • [ 86953-79-9 ]
  • [ 137496-71-0 ]
Reference: [1] Patent: WO2008/73825, 2008, A1,
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