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[ CAS No. 43041-12-9 ] {[proInfo.proName]}

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Chemical Structure| 43041-12-9
Chemical Structure| 43041-12-9
Structure of 43041-12-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 43041-12-9 ]

CAS No. :43041-12-9 MDL No. :MFCD06656665
Formula : C6H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BLWYXBNNBYXPPL-RXMQYKEDSA-N
M.W : 129.16 Pubchem ID :853476
Synonyms :

Calculated chemistry of [ 43041-12-9 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.84
TPSA : 38.33 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) : -7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 0.11
Log Po/w (WLOGP) : -0.47
Log Po/w (MLOGP) : 0.0
Log Po/w (SILICOS-IT) : 0.63
Consensus Log Po/w : 0.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.58
Solubility : 34.1 mg/ml ; 0.264 mol/l
Class : Very soluble
Log S (Ali) : -0.47
Solubility : 43.7 mg/ml ; 0.339 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.85
Solubility : 18.3 mg/ml ; 0.142 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 43041-12-9 ]

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 [ 43041-12-9 ]

* 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 [ 43041-12-9 ]
  • Downstream synthetic route of [ 43041-12-9 ]

[ 43041-12-9 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 43041-12-9 ]
  • [ 498-63-5 ]
Reference: [1] Patent: US6353006, 2002, B1, . Location in patent: Page column 116
  • 2
  • [ 43041-12-9 ]
  • [ 3554-65-2 ]
Reference: [1] Patent: US2012/165352, 2012, A1,
[2] Patent: TWI524893, 2016, B,
  • 3
  • [ 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
  • 4
  • [ 13515-74-7 ]
  • [ 43041-12-9 ]
YieldReaction ConditionsOperation in experiment
96% With ammonium cerium (IV) nitrate; water; acetic acid In dichloromethane at 20℃; for 0.133333 h; Inert atmosphere The substrate (1 equiv) was added to a solution of CAN (20 mol percent) in minimum amount of water (roughly 15 equiv). The reaction mixture was dissolved in dichloromethane and stirred magnetically. Acetic acid (10 equiv) was added to the solution and left to stir at rt for the required time mentioned in Table 2. Upon completion of the reaction, the solvent was evaporated under reduced pressure and worked up in the following methods. Method A: The solid residue was washed twice with petroleum ether to remove the by product trityl alcohol. The residue was then dissolved in methanol and filtered through a short pad of celite. Removal of the solvent under reduced pressure yielded the free amine. Method B: Water and acetic acid were removed from the reaction mixture in vacuo. The residue was dissolved in dry dichloromethane, followed by the addition of triethylamine (2.5 equiv) and acetic anhydride or benzoyl chloride (1.5 equiv). After the completion of the reaction, the solvent was evaporated. The residue was extracted with ethyl acetate twice. The combined organic layer was washed with water and brine and finally dried (Na2SO4). Solvent was removed under reduced pressure and the residue obtained was purified by silica gel column chromatography to afford the acylated amine.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 1, p. 34 - 37
  • 5
  • [ 67-56-1 ]
  • [ 147-85-3 ]
  • [ 43041-12-9 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: at -5 - 25℃; for 2 h;
Stage #2: With potassium carbonate In water at 0℃;
A solution of L-proline (2.23 g) in dry methanol (15 ml) was cooled to -5° C. and thionyl chloride (4.52 g) was added dropwise, while stirring and maintaining the temperature of the reactants below 0° C. The reaction was continued at 25° C. for 2 h. The solvent was distilled and the residue stored in ice-chest for 12 h. The solid mass was added to aqueous solution of potassium carbonate (50percent, 20 ml) at 0° C. and the separated oily layer was extracted into ether (15 ml.x.3). The ethereal layer was dried over anhydrous sodium sulfate and distilled to afford 2.3 g of 2-(carbomethoxy)-pyrrolidine (85percent), [MS (m/z) M+129 (1percent), 114 (0.5), 70(100), 68(50), 43(80), 41(90)]. It was taken in dry diethyl ether (15 ml), cooled to 0° C. and t-butylhypochlorite (2.16 g) added dropwise. The reaction was monitored on silica gel thin layer using chloroform as the eluant. After completion of the reaction (15 min.), potassium t-butoxide (2.24 g) was added gradually over 10 min. and the reactants stirred at 25° C. for 5 h. The solution was filtered and the solvent distilled under reduced pressure to afford 2-(carbomethoxy)-1-pyrrroline (2 g), [MS (m/z) M+ 127(1percent), 112(0.5), 97 (15), 69 (100), 54 (50), 41 (75)]. To a suspension of magnesium turnings (0.43 g) in dry ether, iodine (0.01 g) was added followed by dropwise addition of a solution of methyl iodide (3.08 g) in ether (5 ml) at 35° C. The mixture was stirred until the disappearance of magnesium turnings (15 min), then cooled to 0° C. To it, a solution of 2-(carbomethoxy)-1-pyrrroline (2 g) in dry ether (5 ml) was added over 5 min. and the mixture was stirred at room temperature. On completion of the reaction (2 h) the product was worked up by the addition of dilute hydrochloric acid (5percent, 10 ml) and the organic layer separated. The aqueous layer was further extracted with ether (10 ml.x.2) and the combined organic layers dried over anhydrous sodium sulphate and distilled to afford pure 2-acetyl-1-pyrroline [1.3g, 95percent purity, [MS (m/z) M+ 111 (5percent), 96 (0.1), 83 (15), 69(8), 68 (10), 55 (2), 52 (0.2), 43 (100),42 (25), 41 (50)].To a solution of L-proline (2.23 g) in dry methanol (15 ml) cooled to -5° C., thionyl chloride (4.52 g) was added drop wise, while stirring and maintaining the temperature of the reactants below 0° C. The reaction mixture was allowed to attain room temperature (25° C.) and further stirred for 2 h. The solvent was distilled off from it and the residue stored in ice-chest for 12 h. The solid mass that separated was added to an aqueous potassium carbonate solution (50percent, 20 ml) at 0° C. and the separated oily layer extracted into ether (15 ml.x.3). The combined ethereal layers were dried over anhydrous sodium sulfate and distilled to afford 2.3 g of 2-(carbomethoxy)-pyrrolidine [85percent, MS (m/z) M+129 (1percent), 114 (0.5), 70(100), 68(50), 43(80), 41(90)]. To an ice-cooled solution of the compound in dry diethyl ether (15 ml), t-butylhypochlorite (2.16 g) was added drop-wise. The reaction was monitored on thin layer of silica gel using chloroform as the eluant. After 15 min. anhydrous potassium acetate (2.76 g) was added gradually added to it over 10 min., and the mixture stirred at 25° C., while monitoring the reaction by TLC. At the end of the reaction (3 h), the solution was filtered and the solvent distilled under reduced pressure to afford 2-carbomethoxy)-1-pyrrroline [Yield: 1.9 g, MS (m/z) M+ 127(1percent), 112(0.5), 97 (15), 69,(100), 54 (50), 41 (75)]. To a suspension of magnesium turnings (0.43 g) in dry diethylether, iodine (0.01 g) was added followed by a solution of methyl iodide (3.08 g) in ether (5 ml) dropwise at 35° C. The mixture was stirred until the disappearance of magnesium (15 min) and then after cooling to 0° C., a solution of 2-(carbomethoxy)-1-pyrrroline (1.9 g) in dry diethylether (5 ml) was added over 5 min. On completion of the reaction (2 h) as found by GC, the product was worked up by addition of dilute hydrochloric acid (5percent, 10 ml) and separation of the organic layer. The aqueous layer was further extracted with diethylether (10 ml.x.2) and the combined organic layers dried over anhydrous sodium sulphate. Removal of the solvent afforded pure 2-acetyl-1-pyrroline [1.2 g, 95percent purity, MS (m/z) M+ 111 (5percent), 96 (0.1), 83 (15), 69(8), 68 (10), 55(2), 52 (0.2), 43 (100), 42 (25), 41 (50)].
Reference: [1] Patent: US6723856, 2004, B1, . Location in patent: Page column 4-5
  • 6
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Reference: [1] Synlett, 2002, # 8, p. 1283 - 1284
  • 7
  • [ 147-85-3 ]
  • [ 43041-12-9 ]
Reference: [1] Patent: US6201006, 2001, B1,
  • 8
  • [ 1193-62-0 ]
  • [ 43041-12-9 ]
Reference: [1] Canadian Journal of Chemistry, 2002, vol. 80, # 12, p. 1662 - 1667
  • 9
  • [ 634-97-9 ]
  • [ 43041-12-9 ]
Reference: [1] Canadian Journal of Chemistry, 2002, vol. 80, # 12, p. 1662 - 1667
  • 10
  • [ 24424-99-5 ]
  • [ 43041-12-9 ]
  • [ 145681-01-2 ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine In dichloromethane at 0 - 20℃; for 16 h; 1002721 To a stirring solution of proline methyl ester (70 g, 422 mmol) in CH2C12 (700 mL) were added Et3 (183 mL, 1.26 mol) at 0 °C and stirred for 10 min. After added Boc- anhydride (184 mL, 845 mmol) at 0 °C and the reaction mixture was stirred at RT for 16 h. After consumption of the starting material (by TLC), the reaction was diluted with water (200 mL) and extracted with (( (2 x 200 mL). The combined organic layer was washed with citric acid (1 x 150 mL), brine (1 x 200 mL). The organic layer was dried over a2S04 and concentrated under reduced pressure to afford crude compound which was purified by column chromatography by eluting 50percent EtOAc/w-hexane to obtain 6S-N (80 g, 83percent) as thick syrup. 1H-NMR: (400 MHz, DMSO-d6): δ 4.15-4.13 (m, 1H), 3.65 (s, 3H), 3.35-3.30 (m, 2H), 2.23- 2.15 (m, 1H), 1.86-1.78 (m, 3H), 1.41 (s, 9H); LCMS (m/z): 129 [(M++l)-Boc]
73% With triethylamine In dichloromethane at 0 - 20℃; for 16 h; To a stirred solution of methyl pyrrolidine-2-carboxylate (lntermediate-8) (1 g, 7.74 mmol) in DCM (10 mL) TEA (2.7 mL) was added, followed by di-ie/f-butyl dicarbonate (Boc anhydride, (Boc)20) (1 .86 g, 8.51 mmol) at 0 °C and the reaction mixture was stirred at room temperature for 16 h. The progress of the reaction was monitored by TLC. The reaction mixture was quenched with water (20 mL) and extracted with chloroform (2x20 mL). The combined organic layer was washed with water (10 mL) and brine (10 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude compound was purified by column chromatography (silica gel 100-200 mesh) to afford the title compound (1.3 g, 73percent yield) as pale yellow liquid.
66% With triethylamine In acetonitrile at 0 - 20℃; for 16.1667 h; To stirred solution of methyl prolinate (300 mg, 2.32mmol) in acetonitrile (5 mL) was added triethyl amine (0.55 g, 4.65mmol) and the reaction was stirred for 10 min. Di-t-butyl dicarbonate (0.43 g, 2.78 mmol) was added dropwise to the reaction mixture at 0 °C and stirred for 16 h at ambient temperature. The reaction mixture was concentrated and purified via standard methods to afford 1-(tert-butyl) 2-methyl pyrrolidine-1 ,2-dicarboxylate (0.35 g, 66percent) as pale yellow oil.
Reference: [1] Patent: WO2014/120800, 2014, A1, . Location in patent: Paragraph 00272; page 113
[2] Patent: WO2018/20004, 2018, A1, . Location in patent: Page/Page column 57-58
[3] Patent: WO2016/89977, 2016, A1, . Location in patent: Paragraph 00144
[4] Organic Letters, 2018, vol. 20, # 18, p. 5661 - 5665
[5] Patent: WO2009/146112, 2009, A1, . Location in patent: Page/Page column 40
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  • [ 24424-99-5 ]
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  • [ 73323-65-6 ]
Reference: [1] Patent: US2009/93472, 2009, A1, . Location in patent: Page/Page column 31-32
[2] Patent: US2010/160352, 2010, A1, . Location in patent: Page/Page column 15
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 3, p. 551 - 556
  • 12
  • [ 43041-12-9 ]
  • [ 54503-10-5 ]
Reference: [1] Patent: WO2009/146112, 2009, A1,
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