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Chemical Structure| 664364-48-1 Chemical Structure| 664364-48-1

Structure of 664364-48-1

Chemical Structure| 664364-48-1

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Product Details of [ 664364-48-1 ]

CAS No. :664364-48-1
Formula : C5H11NO
M.W : 101.15
SMILES Code : O[C@@H]1[C@H](C)NCC1
MDL No. :MFCD19218863

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Application In Synthesis of [ 664364-48-1 ]

* 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 [ 664364-48-1 ]

[ 664364-48-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 796600-15-2 ]
  • [ 664364-48-1 ]
  • 2-chloro-4-[(2S,3S)-3-hydroxy-2-methylpyrrolidin-1-yl]-3-methylbenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
114 mg With lithium carbonate; In dimethyl sulfoxide; at 100℃; for 2h; Toan ice-cold solution of (4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one 6 (0.95g, 8.25 mmol) in THF (38 ml) was added dropwise 65-80% Red-Al intoluene (9.21 g), and the mixture was refluxed for 3 h. Aftercooling to 0 C,NaHCO3?10 H2O(3.78g)was added to the reaction mixture at 0 C.After stirring at room temperature for 18 h,the mixture was filteredthroughCeliteand the insoluble material was washed with THF. The filtrate wasconcentrated undervacuum to give pyrrolidine 7(crude, 3.73 g). Amixture of the obtained pyrrolidine 7(1.24 g, <strong>[796600-15-2]2-chloro-4-fluoro-3-methylbenzonitrile</strong>(424 mg, 2.50 mmol) and lithium carbonate (370 mg, 5.00 mmol) inDMSO (12.5 ml) was stirred at 100 C for 2 h. The resultingmixture was cooled to room temperature, and partitioned betweenethyl acetate and water. The organic layer was washed with satd aq.NaCl, dried over Na2SO4, and concentrated invacuo. The residue was purified by silica gel column chromatography(1:0 to 1:1 hexane/EtOAc), and recrystallized with ethylacetate andhexane to give B (114 mg, 18%) as a colorless solid. mp151-153 C; 1H-NMR (300MHz, CDCl3) 1.13(d, J = 6.3Hz, 3H), 1.77 (d, J = 5.1Hz, 1H), 1.98-2.09(m, 2H), 2.34 (s, 3H), 2.86-2.93(m, 1H), 3.72-3.79(m, 1H), 3.88-3.97(m, 1H), 4.35-4.42(m, 1H), 6.80 (d, J = 8.4Hz, 1H), 7.41 (d, J = 8.4Hz,1H); IR (KBr) 2975, 2224, 1586, 1472, 1319cm-1; Anal.Calcd for C13H15ClN2O: C, 62.28; H,6.03; N, 11.17. Found:C, 62.40; H, 6.15; N, 11.14; [alpha]25D -266.8 (c 0.4970, CHCl3).
 

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