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[ CAS No. 642411-11-8 ] {[proInfo.proName]}

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Chemical Structure| 642411-11-8
Chemical Structure| 642411-11-8
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Product Details of [ 642411-11-8 ]

CAS No. :642411-11-8 MDL No. :MFCD17169917
Formula : C16H21NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 291.34 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 642411-11-8 ]

* 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.

  • Downstream synthetic route of [ 642411-11-8 ]

[ 642411-11-8 ] Synthesis Path-Downstream   1~6

  • 2
  • 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone(DMPU, 40 mL) [ No CAS ]
  • [ 67533-12-4 ]
  • [ 642411-11-8 ]
  • ethyl 1-benzylazetidine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
39 Example 39 Example 39 ethyl 1-benzylazetidine-3-carboxylate Tetraethylammonium acetate tetrahydrate (9.42 g) was added to a 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone(DMPU, 40 mL) solution of diethyl 1-benzylazetidine-3,3-dicarboxylate (7.00 g, which was prepared according to the method described in), followed by stirring at 130°C for 12 hours. The reaction solution was added with water, and extracted with an ethyl acetate-hexane (1:1) mixed solvent. The organic layer was washed with water, hexane was added, and extracted with 0.5 mol/L hydrochloric acid. The aqueous layer was washed with tert-butyl methyl ether, and the pH was adjusted to 8 using a 5 mol/L aqueous sodium hydroxide solution, followed by further extraction with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated, to thereby obtain the title compound (3.21 g) having the following physical properties. TLC: Rf 0.54 (hexane:ethyl acetate = 1:2); 1H-NMR(CDCl3): δ 7.11-7.41 (m, 5H), 4.15 (q, J=7.1Hz, 2H), 3.60 (s, 2H), 3.46-3.58 (m, 2H), 3.23-3.41 (m, 3H), 126 (t, J=7.1Hz, 3H).
  • 3
  • [ 20605-01-0 ]
  • [ 100-46-9 ]
  • [ 642411-11-8 ]
YieldReaction ConditionsOperation in experiment
82% [0579] To a solution of diethyl2,2-bis(hydroxymethyl)malonate (4.4 g, 20 mmol) in CH3CN(50 mL) was added Tf20 (7.1 mL, 11.85 g, 42 mmol) at -20 C, followed by two batches ofDIEA (6.45 g, 50 mmol). After 0.5 hr, benzylamine (3.21 g, 35 mmol) was added at -20 C. Themixture was stirred at 70 C for 2 hr. 100 mL of EA and100 mL of brine were added. Organiclayers were dried over Na2S04. Purified by chromatography column on silica gel eluting withPE/EA to afford 4.8 g (82%) of diethyl1-benzylazetidine-3,3-dicarboxylate as a yellow oil. 1HNMR (400 MHz, DMSO-d6) 8 7.29-7.34 (m, 2H), 7.22-7.27 (m, 3H), 4.17 (q, J = 7.2 Hz, 4H),3.56 (s, 2H), 3.51 (s, 4H), 2.39 (s, 3H) and 1.17 (t, J = 7.2 Hz, 6H).
82% With N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In acetonitrile; at -20 - 70℃; for 2.5h; To a solution of diethyl bis-methylolmalonate (4.4 g, 20 mmol) in CH3CN (50 mL) at -20C was added Tf2O (7.1 mL, 11.85 g, 42 mmol) followed by DIEA (6.45 g) in two portions. , 50mmol).After 0.5 hours, benzylamine (3.21 g, 35 mmol) was added at -20C.The mixture was stirred at 70 C for 2 hours.EA (100 mL) and saturated brine (100 mL) were added.The organic phase is dried over Na2SO4.The tannin extract was purified by PE/EA to give 3,3-diethyl 1-benzylazetidine-3,3-dicarboxylate (4.8 g, 82%) as a yellow oil.
A solution of <strong>[20605-01-0]diethyl 2,2-bis(hydroxymethyl)malonate</strong> 24 (7.01 g, 31.83 mmol, 1.0 eq.) in anhydrous acetonitrile (105 ml) was cooled to 15 C. Triflic anhydride (11.25 ml, 66.84 mmol, 2.1 eq.) was added drop-wise while keeping the temperature below 10 C. N,N-Diisopropylethylamine (27.72 ml, 159.2 mmol, 5.0 eq.) wasthen added drop-wise while maintaining the temperature below 10 C. After the addition the temperature was raised to rt. Benzylamine (5.22 ml, 47.8 mmol, 1.5 eq.) was added in a singleportion. The resulting mixture was heated to 70 C and stirred for3 h. The reaction mixture was cooled to ambient temperature,diluted with toluene (40 ml) and washed with brine (2 500 ml).The separated organic layer was dried over anhydrous sodium sulphate. The solvent was evaporated in vacuo to afford the crude product, diethyl 1-benzylazetidine-3,3-dicarboxylate 25 as a dark brown oil (5.59 g, 60%) which was used directly in the next step. Rf 0.80 (25% hexane:ethyl acetate); numax (neat)/cm -1 2981, 1729,1270, 1154, 1013, 857, 700; 1H NMR (300 MHz, CDCl3); delta 7.34e7.20(m, 5H, ArH's), 4.25 (q, 2H, J 7.1 Hz, OCH2CH3), 4.23 (q, 2H,J 7.1 Hz, OCH2CH3), 3.66 (s, 6H, CH2Ph 2 CH2N), 1.28 (t, 3H,J 7.1 Hz, OCH2CH3), 1.26 (t, 3H, J 7.1 Hz, OCH2CH3); 13C NMR (75 MHz, CDCl3); delta 169.93, 137.22, 128.66, 128.52, 127.38, 62.91,62.00, 59.65, 49.61, 14.12; HRMS m/z (ESI) 292.1632 ([M + H]+ requires 292.1543).
2.7 g To a mixture of compound 9-2 (8g, 36.33mmol, l.Oeq) in MeCN (160mL) was added Tf20 (21.52g, 76.29mmol, 2.1eq) at -20C, followed by DIEA (23.48g, 181.64mmol, 5.0eq). After 0.5h, BnNH2 was added at -20C. The mixture was stirred for 2h at 70C. EA (200mL) and brine (lOOmL) were added. The organic layer was dried over Na SO . filtered and concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel (PE: EA = 20: 1) to give the tile compound (2.7 g). LC-MS: [M+H]+ = 292.3.

  • 4
  • [ 642411-11-8 ]
  • [ 94985-27-0 ]
  • 5
  • [ 642411-11-8 ]
  • [ 1016233-08-1 ]
  • 6
  • [ 642411-11-8 ]
  • [ 1011479-75-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen; hydrogenchloride; 20% palladium hydroxide-activated charcoal / water; 1,4-dioxane; ethanol / 144 h / 20 °C 2: sodium hydrogencarbonate / water; 1,4-dioxane / 24 h / 20 °C
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