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[ CAS No. 1723-00-8 ] {[proInfo.proName]}

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Chemical Structure| 1723-00-8
Chemical Structure| 1723-00-8
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Product Details of [ 1723-00-8 ]

CAS No. :1723-00-8 MDL No. :MFCD00064346
Formula : C6H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HXEACLLIILLPRG-RXMQYKEDSA-N
M.W : 129.16 Pubchem ID :736316
Synonyms :
D-Pipecolinic acid

Calculated chemistry of [ 1723-00-8 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 37.33
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) : -8.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.17
Log Po/w (XLOGP3) : -2.31
Log Po/w (WLOGP) : -0.17
Log Po/w (MLOGP) : -2.21
Log Po/w (SILICOS-IT) : 0.46
Consensus Log Po/w : -0.61

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.88
Solubility : 981.0 mg/ml ; 7.59 mol/l
Class : Highly soluble
Log S (Ali) : 1.81
Solubility : 8340.0 mg/ml ; 64.6 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.42
Solubility : 48.5 mg/ml ; 0.376 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 1723-00-8 ]

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 [ 1723-00-8 ]

* 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 [ 1723-00-8 ]
  • Downstream synthetic route of [ 1723-00-8 ]

[ 1723-00-8 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 1723-00-8 ]
  • [ 3197-44-2 ]
Reference: [1] Journal of the American Chemical Society, 1995, vol. 117, # 36, p. 9369 - 9370
[2] Journal of Organic Chemistry, 1997, vol. 62, # 15, p. 5023 - 5033
[3] Journal of the American Chemical Society, 1999, vol. 121, # 4, p. 700 - 709
[4] Tetrahedron, 2013, vol. 69, # 48, p. 10311 - 10315
  • 2
  • [ 50-00-0 ]
  • [ 1723-00-8 ]
  • [ 41447-17-0 ]
YieldReaction ConditionsOperation in experiment
100% With 5%-palladium/activated carbon; hydrogen In methanol; water for 20 h; 37percent Aqueous solution of formaldehyde (1.26 mL, 16.9 mmol) was added to a mixture of (2R)-piperidine-2-carboxylic acid (2.00 g, 15.5 mmol) and 5percent Pd/C (500 mg) in MeOH (20 mL).
After the reaction mixture was purged with H2 gas, additional formaldehyde (0.60 mL, 8.06 mmol) was added, and stirred under H2 atmosphere for 20 h.
The reaction mixture was filtered through a pad of Celite, and washed with MeOH (200 mL).
The filtrate was concentrated by rotary evaporation to afford analytically pure amino acid 8 (2.23 g, quantitative yield) as a white solid, which was used in the next step without further purification. TLC: Rf 0.25 (1:1 CH2Cl2/MeOH). Mp: 208-210 °C. [α]D27.1 = + 67.6 (c 1.27, MeOH). IR (KBr, film): 3407, 2950, 1615, 1399 cm-1. 1H NMR (400 MHz, CDCl3): d8.22 (br s, 1H), 3.64 (d, 1H, J = 12.0 Hz), 3.28 (m, 1H), 2.86 (s,3H), 2.70 (m, 1H), 2.34 (d, 1H, J = 14.4 Hz), 2.00–1.74 (m, 4H),1.46 (m, 1H). 13C NMR (100 MHz, DMSO-d6): d 170.4, 68.3, 53.3,42.3, 28.0, 23.1, 21.8. HRMS (ESI) m/z calculated for C7H13NO2143.0946, found 143.0947.
90% With palladium 10% on activated carbon; hydrogen In methanol; water To a solution of D-pipecolinic acid (10.0 g, 77.4 mmol, 1.0 eq.) in methanol (100 mL) was added formaldehyde (37percent aqueous solution, 30.8 mL, 154.8 mmol, 2.0 eq.), followed by Pd/C (10 wtpercent, 1.0 g). The reaction mixture was stirred under H2 (1 atm) overnight, and then filtered through Celite, with washing of the filter pad with methanol. The filtrate was concentrated under reduced pressure to afford compound 126 (10.0 g, 90percent yield) as a white solid.
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6827 - 6843
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 43, p. 7235 - 7239
[3] Patent: WO2016/59622, 2016, A2, . Location in patent: Page/Page column 95-96
[4] Journal of Organic Chemistry, 2016, vol. 81, # 21, p. 10302 - 10320
[5] Patent: WO2018/86139, 2018, A1, . Location in patent: Page/Page column 143
[6] Journal of the American Chemical Society, 2006, vol. 128, # 50, p. 16018 - 16019
  • 3
  • [ 24424-99-5 ]
  • [ 1723-00-8 ]
  • [ 28697-17-8 ]
YieldReaction ConditionsOperation in experiment
87.8% With sodium hydrogencarbonate In methanol at 20℃; for 24 h; To a 1000 mL round bottom flask, 2R-piperidine carboxylic acid (8.0 g, 0.062 mol), di-tert-butyl dicarbonate (14.8 g, 0.068 mol), sodium bicarbonate (26.04 g, 0.310 mol) and methanol (400 mL) were added, and stirred at room temperature for 24 hours. Thereafter, the reaction product was subjected to vacuum distillation for removal of methanol, dissolved with water, washed 3 times with ethyl ether, adjusted to pH = 2 with saturated potassium hydrogen sulfate, and extracted 3 times with dichloromethane. The extracts were combined, washed 3 times with saturated brine, concentrated, and separated through a silica gel column (eluent: petroleum ether/ethyl acetate/acetic acid), to give 12.48 g of a white product, yield 87.8percent. [0075] 1H-NMR (400 MHz, DMSO) δ ppm: 12.71 (1H, s), 4.61 (1H, d, J = 28.8 Hz), 3.82 (1H, d, J = 12 Hz), 2.93 (1H, m), 2.06 (1H, s), 1.62 (3H, m), 1.39(11H, m); EI-MS (m/z): 229.1[M]+.
87.8% With sodium hydrogencarbonate In methanol at 20℃; for 24 h; To a 1000 mL round bottom flask, 2R-piperidine carboxylic acid (8.0 g, 0.062 mol), di-tert-butyl dicarbonate (14.8 g, 0.068 mol), sodium bicarbonate (26.04 g, 0.310 mol) and methanol (400 mL) were added, and stirred at room temperature for 24 hours. Thereafter, the reaction product was subjected to vacuum distillation for removal of methanol, dissolved with water, washed 3 times with ethyl ether, adjusted to pH=2 with saturated potassium hydrogen sulfate, and extracted 3 times with dichloromethane. The extracts were combined, washed 3 times with saturated brine, concentrated, and separated through a silica gel column (eluent: petroleum ether/ethyl acetate/acetic acid), to give 12.48 g of a white product, yield 87.8percent.1H-NMR (400 MHz, DMSO) δ ppm: 12.71 (1H, s), 4.61 (1H, d, J=28.8 Hz), 3.82 (1H, d, J=12 Hz), 2.93 (1H, m), 2.06 (1H, s), 1.62 (3H, m), 1.39(11H, m); EI-MS (m/z): 229.1[M]+.
83% With triethylamine In 1,4-dioxane; water at 20℃; for 20 h; To a suspension of (R)-piperidine-2-carboxylic acid (12.5 g, 96.8 mmol) in water (88mL) and 1,4-dioxane (133 mL), were added di-tert-butyl dicarbonate (23.2 g, 106 mmol) andtriethylamine (13.5 mL, 96.8 mmol). The solution was stirred at room temperature for 20hours. The mixture was concentrated in vacuo, diluted with ethyl acetate (200 mL) and25 washed with 5percent aqueous HCl. The organic phase was separated, dried over anhydrousNa2S04, filtered, and concentrated to afford the compound as a white solid (18.5 g, 83percent).MS 130 (MH+- boc).
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 591 - 601
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 9, p. 1550 - 1557
[3] ChemMedChem, 2013, vol. 8, # 4, p. 577 - 581
[4] Patent: EP2805947, 2014, A1, . Location in patent: Paragraph 0074-0075
[5] Patent: US2015/126500, 2015, A1, . Location in patent: Paragraph 0127; 0128
[6] Patent: WO2014/25706, 2014, A1, . Location in patent: Page/Page column 73
[7] Journal of the American Chemical Society, 1995, vol. 117, # 32, p. 8488 - 8489
[8] Patent: US2004/198701, 2004, A1, . Location in patent: Page/Page column 10
[9] Patent: US2005/227969, 2005, A1, . Location in patent: Page/Page column 10
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  • [ 28697-17-8 ]
Reference: [1] Patent: WO2012/117048, 2012, A1, . Location in patent: Page/Page column 52-53
  • 5
  • [ 58632-95-4 ]
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  • [ 28697-17-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 1998, vol. 33, # 1, p. 23 - 31
  • 6
  • [ 67-56-1 ]
  • [ 1723-00-8 ]
  • [ 18650-38-9 ]
Reference: [1] ChemMedChem, 2013, vol. 8, # 4, p. 577 - 581
[2] Tetrahedron Letters, 1991, vol. 32, # 49, p. 7183 - 7186
[3] Tetrahedron Letters, 1990, vol. 31, # 16, p. 2341 - 2344
[4] Chemistry - A European Journal, 2010, vol. 16, # 13, p. 3970 - 3982
[5] Patent: US2016/2251, 2016, A1, . Location in patent: Paragraph 1328
  • 7
  • [ 1723-00-8 ]
  • [ 68474-13-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 20, p. 6386 - 6392
  • 8
  • [ 1723-00-8 ]
  • [ 688809-99-6 ]
Reference: [1] Patent: WO2012/117048, 2012, A1,
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