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Structure of 936850-09-8

Chemical Structure| 936850-09-8

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Product Details of [ 936850-09-8 ]

CAS No. :936850-09-8
Formula : C10H16N2O2
M.W : 196.25
SMILES Code : O=C(N1CC(C)(C#N)C1)OC(C)(C)C
MDL No. :MFCD17016128

Safety of [ 936850-09-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 936850-09-8 ]

* 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 [ 936850-09-8 ]

[ 936850-09-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 936850-09-8 ]
  • [ 887591-62-0 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In methanol; water; for 4.0h;Reflux; [Note: Since cyanoazetidine 26 is volatile, acombined procedure designed to maximize the yield is provided here. However, if azetidine 26 is already inhand, follow just the NaOH hydrolysis step.] To a solution of tert-butyl 3-cyanoazetidine-1-carboxylate (22)(150 mg, 0.823 mmol, 1 equiv.) in dry THF (3 mL) was added LiHMDS (1M in THF, 0.905 mL, 0.905 mmol, 1.1equiv.) at ?78 oC and stirred for 30 min. at the same temperature. Methyl iodide (77 muL, 1.23 mmol, 1.5 equiv.)was added via syringe and stirred at ?78 oC for 45 min. followed by stirring at rt for 1 h. The resulting mixturewas quenched with NH4Cl (2 mL) and extracted with ethyl acetate (3 x 2 mL). The combined organic extractswere washed with brine (3 mL), dried over Na2SO4, and concentrated. Compound 26 was used in the next stepwithout further purification. A solution of NaOH (115 mg, 4.12 mmol, 5 equiv.) in H2O (3 mL) was slowly addedto a solution of tert-butyl 3-cyano-3-methylazetidine-1-carboxylate (26) in MeOH (3 mL) and then refluxeduntil judged complete by TLC (ca. 4 h). The reaction mixture was cooled to rt and the MeOH was removed in vacuo. The mixture was neutralized with 10 percent aq. citric acid (3 mL) and extracted with CH2Cl2 (3 x 10 mL). Thecombined organic layers were washed with brine (50 mL), dried over Na2SO4, and concentrated to give thedesired product 27 (107.5 mg, 61percent for 2 steps). Physical State: white crystalline solid (mp 135?136 oC); 1HNMR (500 MHz, CDCl3): [mixture of rotamers] delta 6.71 (br s, 1H, COOH minor rotamer), 5.91 (br s, 1H, COOHmajor rotamer), 4.25 (d, J 8.5 Hz, 2H, major), 4.19 (d, J 8.4 Hz, 2H, minor), 3.69 (d, J 8.5 Hz, 2H, minor), 3.68 (d,J 8.6 Hz, 2H, major), 1.55 (s, 3H), 1.44 (s, 9H); 13C NMR (126 MHz, CDCl3): [mixture of rotamers] delta 179.3(major), 178.5 (minor), 156.6 (minor), 156.5 (major), 80.3 (minor), 80.1 (major), 58.5 (br, major + minor, 2 x2C), 39.1 (minor), 38.7 (major), 28.5 (major, 3C), 28.5 (minor, 3C), 23.1 (minor), 22.6 (major); HRMS (ESI-TOF):calc?d for C10H16NO4 [M-H] 214.1079; found 214.1080.
 

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