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[ CAS No. 65709-33-3 ] {[proInfo.proName]}

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Chemical Structure| 65709-33-3
Chemical Structure| 65709-33-3
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Product Details of [ 65709-33-3 ]

CAS No. :65709-33-3 MDL No. :MFCD05864674
Formula : C10H13FN2 Boiling Point : -
Linear Structure Formula :- InChI Key :NZAKSEMIIIZYEM-UHFFFAOYSA-N
M.W : 180.22 Pubchem ID :4617623
Synonyms :

Safety of [ 65709-33-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 65709-33-3 ]

* 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 [ 65709-33-3 ]
  • Downstream synthetic route of [ 65709-33-3 ]

[ 65709-33-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 403-32-7 ]
  • [ 107-15-3 ]
  • [ 65709-33-3 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: for 4 h;
Stage #2: With sodium tetrahydroborate In ethanol at 20℃;
A solution of ethylene diamine (7.4 g, 123.5 mmol) in ethanol (100 mL) was added dropwise over 15 minutes to a stirring solution of A- fluoroglyoxal (21.0 g, 123.5 mmol) in ethanol (300 mL) and the reaction was left for 4 hours. Sodium borohydride (23.5 g, 622 mmol) was added and the mixture was stirred overnight at room temperature. Water (200 mL) was added and the mixture was stirred for 1 hour after which the majority of the ethanol was removed in vacuo. The concentrated solution was extracted with DCM (4 x 100 mL) and the combined extracts were combined, washed with brine and dried over Na2SO4. The solvent was removed in vacuo to yield a pale yellow solid (19.0 g, 86percent). 8.8 g of this material was dissolved in methanol (60 mL) and added to a solution of iV-acetyl-L-leucine (16.5 g, 95.2 mmol) in methanol (100 mL). Ethyl acetate (550 mL) was added and the mixture was left at room temperature overnight. The precipitate was filtered and dried to give a solid (9.0 g) which was taken up in 4M NaOH aq. (100 mL) and extracted with DCM (4 x 100 mL). The combined extracts were combined, washed with brine and the solvent was removed in vacuo to yield a solid (3.1 g). This solid was re-crystallized from EtOAc to yield 2.23 g of the S enantiomer (the title compound). The enantiomeric excess was determined by chiral chromatography employing the following chiral chromatographic conditions: Column: Phenomenex Chirex (S)-ICR 250 x 4.6 mm; solvent: n-heptane:ethanol [80:20] + 0.3percent TFA; L = 254 nm, flow rate = 1 mL/min, UV sensitivity = 0.1 AUF; ~1 mg of compound in 1 mL of n-heptane: ethanol [75:25] using authentic chiral compounds and racemate as reference.
Reference: [1] Patent: WO2006/86705, 2006, A1, . Location in patent: Page/Page column 58
  • 2
  • [ 1421005-03-9 ]
  • [ 65709-33-3 ]
YieldReaction ConditionsOperation in experiment
89% With palladium on activated charcoal; hydrogen In methanol for 4 h; General procedure: Olefins 1 (1 mmol) were dissolved in dry THF (15 mL) under N2 and HgO·2HBF4 (1.1 mmol) was added portionwise followed by the addition of N,N′-disubstitutedethylene diamine 2 (1.5 mmol). The reaction mixture was stirred at 70 °C for the appropriate time as shown in Table 1. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with water and extracted with CH2Cl2 (3 × 30 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo, and purified by flash column chromatography on silica gel to afford corresponding protected piperazine derivatives 3. The compound 3 was dissolved in MeOH (9 mL) containing acetic acid (1 mL) and then added Pd/C.27 The reaction mixture was stirred for 4 h under H2 on a Parr hydrogenator and the progress of the reaction was monitored on TLC. After completion of reaction, the catalyst was filtered off and the organic mixture was evaporated in a rota-vapour. The crude mixture was purified by column chromatography using chloroform:methanol (95:5–80:20) as eluting mixture to get the corresponding product 4. The products reported herein, were characterized by 1H NMR, 13C NMR, and mass spectroscopy. The spectroscopic data of the compounds are in agreement with those reported in the literature.29 Spectral data for 3a29a–d. 1H NMR (400 MHz, CDCl3): δ 1.92–2.14 (m, 4H), 2.14–2.66 (m, 2H), 3.82 (s, 4H), 4.14 (m, 1H), 7.01–7.49 (m, 15H); 13C NMR: δ 29.4, 36.5, 41.4, 62.5, 125.80, 127.40, 128.41, 144.70; MS (ESI): 342 (M+).
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 8, p. 761 - 764
  • 3
  • [ 939975-25-4 ]
  • [ 65709-33-3 ]
YieldReaction ConditionsOperation in experiment
3.8 g With palladium 10% on activated carbon; hydrogen In ethanol; water for 24 h; General Procedure for Examples 3j to 3p (Racemic Mixture) Synthesis: [0238] Example 3b to 3h are dissolved into the solvent, catalyst (10percent w/w) is added and the resulting mixture is hydrogenated using a Parr equipment (starting pH2 4 bar) until reaction is complete. The mixture is filtered over a celite pad, the filtrate is concentrated under reduced pressure and the residue is used without further purification (for reactions performed in acetic acid the residue is then partitioned between DCM and aqueous NaOH and concentrated under reduced pressure).
3.8 g With palladium 10% on activated carbon; hydrogen In ethanol; water for 24 h; General procedure: Example 3b to 3h are dissolved into the solvent, catalyst (10percent w/w) is added and theresulting mixture is hydrogenated using a Parr equipment (starting pH2 4 bar) until reactionis complete. The mixture is filtered over a celite pad, the filtrate is concentrated under reduced pressure and the residue is used without further purification (for reactions performed in acetic acid the residue is then partitioned between DCM and aqueous NaOH and concentrated under reduced pressure).
Reference: [1] Patent: US2015/105397, 2015, A1, . Location in patent: Paragraph 0238
[2] Patent: WO2015/55698, 2015, A1, . Location in patent: Page/Page column 54
  • 4
  • [ 712-40-3 ]
  • [ 65709-33-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732
  • 5
  • [ 32222-45-0 ]
  • [ 65709-33-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732
  • 6
  • [ 7550-03-0 ]
  • [ 65709-33-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732
  • 7
  • [ 1813-94-1 ]
  • [ 65709-33-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732
  • 8
  • [ 460-00-4 ]
  • [ 65709-33-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732
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