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[ CAS No. 609-36-9 ] {[proInfo.proName]}

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Chemical Structure| 609-36-9
Chemical Structure| 609-36-9
Structure of 609-36-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 609-36-9 ]

CAS No. :609-36-9 MDL No. :MFCD00005250
Formula : C5H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 115.13 Pubchem ID :-
Synonyms :
H-DL-Pro-OH

Calculated chemistry of [ 609-36-9 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 32.52
TPSA : 49.33 Ų

Pharmacokinetics

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) : -8.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.84
Log Po/w (XLOGP3) : -2.5
Log Po/w (WLOGP) : -0.56
Log Po/w (MLOGP) : -2.59
Log Po/w (SILICOS-IT) : 0.22
Consensus Log Po/w : -0.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 1.09
Solubility : 1410.0 mg/ml ; 12.2 mol/l
Class : Highly soluble
Log S (Ali) : 2.01
Solubility : 11700.0 mg/ml ; 102.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.13
Solubility : 85.7 mg/ml ; 0.745 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 609-36-9 ]

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 [ 609-36-9 ]

* 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 [ 609-36-9 ]
  • Downstream synthetic route of [ 609-36-9 ]

[ 609-36-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 609-36-9 ]
  • [ 498-63-5 ]
YieldReaction ConditionsOperation in experiment
65% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 70℃; Inert atmosphere DL-Proline (6.0 g, 52.0 mmol) was added slowly and portion wise to a stirred suspension of LiAIH4 (3.0 g, 78.0 mmol) in THF (80 ml_) at 0 °C under nitrogen atmosphere carefully over a period of 30 minutes. The reaction mixture was warmed to room temperature and then heated to reflux for 3 h. The mixture was quenched with 20percent KOH solution at 0 °C slowly (18 - 20 mL). The mixture was filtered through a Celite™ pad and washed ith THF. The filtered precipitate was again refluxed with THF for 30 minutes and filtered. The combined filtrates were concentrated to give K1 as pale yellow liquid which is slowly converts to dark brown liquid (3.2 g, 65percent). Rf: 0.1 (10percent MeOH in DCM & 1 drop AcOH, ninhydrin active).
18%
Stage #1: With thionyl chloride In methanol at 0 - 20℃;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃;
Stage #3: With potassium hydroxide In tetrahydrofuran
To a solution of DL-proline (10Og, 869 mmol) in MeOH (1500 mL) was slowly added SOCl2 at 0 0C. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to give the crude material that was dissolved in THF (1700 mL) again. To this mixture was added portionwise LiAlH4 (132 g, 3.47 mol) at 0 0C. The resulting mixture was heated at 60 0C overnight. The excess LiAlH4 was quenched with KOH. The reaction mixture was filtered and the solid was washed with MeOH (1000 mL). The combined organic layers were dried, filtered, and concentrated under reduced pressure to give the crude material that was purified by distillation to afford 15.8 g (18percent) of pyrrolidin-2-ylmethanol.
Reference: [1] Tetrahedron, 2010, vol. 66, # 40, p. 7970 - 7974
[2] Patent: WO2015/181676, 2015, A1, . Location in patent: Page/Page column 166-167
[3] Patent: WO2011/22508, 2011, A2, . Location in patent: Page/Page column 59
[4] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1931, vol. 203, p. 279,285
[5] Monatshefte fuer Chemie, 1952, vol. 83, p. 541
[6] Patent: EP2202223, 2010, A1, . Location in patent: Page/Page column 72-73
[7] Journal of the American Chemical Society, 2016, vol. 138, # 16, p. 5433 - 5440
  • 2
  • [ 609-36-9 ]
  • [ 3554-65-2 ]
Reference: [1] Patent: US2012/165352, 2012, A1,
[2] Patent: TWI524893, 2016, B,
  • 3
  • [ 108-24-7 ]
  • [ 609-36-9 ]
  • [ 1074-79-9 ]
Reference: [1] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 4, p. 505 - 516
[2] Tetrahedron, 1987, vol. 43, # 10, p. 2285 - 2292
  • 4
  • [ 123-75-1 ]
  • [ 64-18-6 ]
  • [ 59378-87-9 ]
  • [ 56-40-6 ]
  • [ 609-36-9 ]
Reference: [1] Chemistry Letters, 1980, p. 73 - 76
  • 5
  • [ 123-75-1 ]
  • [ 141-53-7 ]
  • [ 59378-87-9 ]
  • [ 56-40-6 ]
  • [ 609-36-9 ]
Reference: [1] Chemistry Letters, 1980, p. 73 - 76
  • 6
  • [ 67-56-1 ]
  • [ 609-36-9 ]
  • [ 43041-12-9 ]
YieldReaction ConditionsOperation in experiment
98% for 16 h; Reflux To a stirred solution of pyrrolidine-2-carboxylic acid (1 g, 8.69 mmol) in MeOH (10 mL) thionyl chloride (0.75 mL, 10.43 mmol) was added and the reaction mixture was stirred at reflux temperature for 16 h. The progress of the reaction was monitored by TLC. The reaction mixture was concentrated, the residue was diluted with DCM (15 mL), the excess of thionyl chloride was quenched with solid NaHC03, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound (1 .1 g, 98percent yield) as pale yellow solid.
90% at 0 - 20℃; for 16 h; Thionyl chloride (3 mL) was added dropwise at 0 °C to a stirred solution of [DL]-proline (1 g, 8.6 mmol) in methanol (15 mL). The reaction was stirred at room temperature for 16 h. The reaction was monitored by TLC. After completion of the reaction, the mixture was concentrated and purified via standard methods to afford methyl prolinate as an off- white solid (1 g, 90percent).
Reference: [1] Patent: WO2018/20004, 2018, A1, . Location in patent: Page/Page column 57
[2] Patent: WO2016/89977, 2016, A1, . Location in patent: Paragraph 00143
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 16, p. 5616 - 5624
[4] Chemistry Letters, 1982, p. 745 - 748
[5] Journal of Agricultural and Food Chemistry, 1993, vol. 41, # 9, p. 1458 - 1461
[6] Phytochemistry, 1999, vol. 52, # 8, p. 1739 - 1744
[7] Chinese Chemical Letters, 2011, vol. 22, # 6, p. 738 - 740
[8] Rapid Communications in Mass Spectrometry, 2011, vol. 25, # 20, p. 2995 - 3011
[9] Patent: US2012/165352, 2012, A1, . Location in patent: Page/Page column 29-30
[10] Food Chemistry, 2015, vol. 168, p. 327 - 331
[11] Food Chemistry, 2015, vol. 168, p. 327 - 331
[12] Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 10892 - 10903
[13] Patent: TWI524893, 2016, B, . Location in patent: Page/Page column 56
[14] Patent: WO2009/146112, 2009, A1, . Location in patent: Page/Page column 40
  • 7
  • [ 501-53-1 ]
  • [ 609-36-9 ]
  • [ 6404-31-5 ]
  • [ 1148-11-4 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2000, vol. 43, # 5, p. 449 - 461
  • 8
  • [ 609-36-9 ]
  • [ 170491-63-1 ]
Reference: [1] Patent: WO2011/22508, 2011, A2,
  • 9
  • [ 609-36-9 ]
  • [ 145681-01-2 ]
Reference: [1] Patent: WO2014/120784, 2014, A1,
[2] Patent: WO2014/120783, 2014, A1,
[3] Patent: WO2016/89977, 2016, A1,
[4] Patent: WO2018/20004, 2018, A1,
[5] Patent: WO2007/122410, 2007, A1,
[6] Patent: WO2009/146112, 2009, A1,
  • 10
  • [ 609-36-9 ]
  • [ 54503-10-5 ]
Reference: [1] Patent: WO2009/146112, 2009, A1,
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