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Chemical Structure| 757239-60-4 Chemical Structure| 757239-60-4
Chemical Structure| 757239-60-4

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Synonyms: Methyl 1-Cbz-azetidine-3-carboxylate

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Product Details of Methyl 1-Cbz-azetidine-3-carboxylate

CAS No. :757239-60-4
Formula : C13H15NO4
M.W : 249.26
SMILES Code : O=C(N1CC(C(OC)=O)C1)OCC2=CC=CC=C2
Synonyms :
Methyl 1-Cbz-azetidine-3-carboxylate
MDL No. :MFCD11110708
InChI Key :VMBHUIMZBSWWCN-UHFFFAOYSA-N
Pubchem ID :45072502

Safety of Methyl 1-Cbz-azetidine-3-carboxylate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Methyl 1-Cbz-azetidine-3-carboxylate

* 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 [ 757239-60-4 ]

[ 757239-60-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 100202-39-9 ]
  • [ 501-53-1 ]
  • [ 757239-60-4 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 18 h; A round bottomed flask containing methyl azetidine-3-carboxylate hydrochloride(3 g, 20 mmol), THF (30 mL) and H20 (30 mL) was added with an aqueous solution ofNaOH (4 M, 5 mL, 20 mmol) at 0 °C, followed by benzyl chloroformate (2.84 mL, 20 mmol). The reaction was vigorously stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between Et20 (100 mL) and H20 (30 mL). The aqueous phase was back-extracted withEt20 (3 x 50 mL), the combined organic phases were dried (Na2SO4) and concentrated in vacuo to give the title compound (5 g, 99percent) as a colourless oil, which was used in subsequent steps without further purification.‘H NMR (400 MHz, CDC13): ö 7.43-7.25 (m, 5 H), 5.10 (s, 2 H), 4.23-4.13 (m, 4 H), 3.74 (s, 3 H), 3.38 (q, J = 7.2 Hz, 1 H).
References: [1] Patent: WO2016/177849, 2016, A1, . Location in patent: Page/Page column 74; 75.
[2] Patent: US2011/183960, 2011, A1, . Location in patent: Page/Page column 27.
  • 2
  • [ 97628-92-7 ]
  • [ 18107-18-1 ]
  • [ 757239-60-4 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: at 0℃;
Stage #2: With acetic acid In methanol; hexanes; toluene
1-BENZYLOXYCARBONYL-3-AZETIDINECARBOXYLIC acid (from step (i); 9.3g, 39. 6MMOL) was dissolved in methanol (LOOML) and toluene (100mL), and cooled to 0°C. A solution of 2M trimethylsilyldiazomethane in hexanes was then added dropwise until bubbling had ceased and the yellow colour persisted. Acetic acid was then added dropwise until the yellow colour disappeared. Concentration of the solution yielded the title compound as an oil (9.48G, 38mmol, 96percent). IH NMR (400MHZ, CDC13) : 8 7.36-7. 31 (5H, m), 5.10 (2H, s), 4.19 (4H, D, J7. 8Hz), 3.75 (3H, s), 3.39 (1H, quintet, J 7. 8HZ).
References: [1] Patent: WO2004/78750, 2004, A1, . Location in patent: Page 81.
  • 3
  • [ 186581-53-3 ]
  • [ 97628-92-7 ]
  • [ 757239-60-4 ]
YieldReaction ConditionsOperation in experiment
98% at 20℃; for 4 h; EXAMPLE 27B; 1-benzyl 3-methylazetidine-1,3-dicarboxylate A solution of Example 27A (4.8 g, 20.3 mmol) in ether (100 ml) was treated with diazomethane (100 ml in ether, 60 mmol) at room temperature for 4 hours. Removal of the volatiles gave Example 27B (4.8 g Yield: 98percent). MS (DCI/NH3) m/z 250 (M+H)+.
References: [1] Patent: US2006/229289, 2006, A1, . Location in patent: Page/Page column 19.
 

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