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[ CAS No. 642411-11-8 ]

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2D
Chemical Structure| 642411-11-8
Chemical Structure| 642411-11-8
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Product Details of [ 642411-11-8 ]

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

Computed Properties of [ 642411-11-8 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 642411-11-8 ]

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Application In Synthesis of [ 642411-11-8 ]

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

[ 642411-11-8 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 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.

  • 3
  • [ 642411-11-8 ]
  • [ 94985-27-0 ]
  • 4
  • [ 642411-11-8 ]
  • [ 1016233-08-1 ]
  • 5
  • [ 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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