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Chemical Structure| 188846-98-2 Chemical Structure| 188846-98-2

Structure of 188846-98-2

Chemical Structure| 188846-98-2

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Product Details of [ 188846-98-2 ]

CAS No. :188846-98-2
Formula : C19H21NO5S
M.W : 375.44
SMILES Code : O=C(N1CC(OS(=O)(C2=CC=C(C)C=C2)=O)CC1)OCC3=CC=CC=C3
MDL No. :MFCD18207681

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Application In Synthesis of [ 188846-98-2 ]

* 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 [ 188846-98-2 ]

[ 188846-98-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 95656-88-5 ]
  • [ 98-59-9 ]
  • [ 188846-98-2 ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 0 - 20℃; for 20h; Reference Example 79 To a mixture of benzyl 3-hydroxy-1-pyrrolidine carboxylate (5.00 g) and pyridine (50 mL) was added p-toluenesulfonyl chloride (4.74 g) at 0C. After the mixture was stirred at room temperature for 20 hours, the reactant was poured into water and extracted with ethyl acetate. The extracts were washed with 1 N hydrochloric acid, a sodium hydrogen carbonate solution and brine, dried and concentrated. The obtained residue was purified by silica gel column chromatography to obtain benzyl 3-[[(4-methylphenyl)sulfonyl]oxy]-1-pyrrolidine carboxylate (4.98 g). 1H-NMR (300 MHz, CDCl3) delta: 1.95-2.24 (2H, m), 2.45 (3H, d, J=2.7 Hz), 3.45-3.64 (4H, m), 5.05-5.12 (3H, m), 7.33-7.36 (7H, m), 7.77-7.80 (2H, m).
  • 2
  • [ 95656-88-5 ]
  • [ 188846-98-2 ]
YieldReaction ConditionsOperation in experiment
13.4 g (66%) In pyridine; p-toluenesulfonyl chloride; B. Twelve grams (54.2 mmol) of <strong>[95656-88-5]benzyl 3-hydroxypyrrolidine-1-carboxylate</strong> were dissolved in 150 mL of pyridine. This solution was cooled to 0C in an ice/water bath and 23.66 g (124.5 mmol) of p-toluenesulfonyl acid chloride were added at once. The reaction was allowed to stand at refrigerator temperatures for 18 hours and then acidified with 5N hydrochloric acid to pH<2. This residue was extracted with ethyl acetate (4x200 mL). The extracts were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel with 50% ethyl acetate/hexane and the product eluted to give 13.4 g (66%) of benzyl 3-(p-methylbenzenesulfonyloxy)pyrrolidine-1-carboxylate as an orange oil. Rf = 0.49 (1/1 hexanes/ethyl acetate); Mass Spectrum (FD+): M+= 375; IR (CHCl3, cm-1): 815, 837, 899, 953, 1020, 1050, 1086, 1115, 1175, 1307, 1359, 1425, 1452, 1497, 1600, 1699, 2897, 3692; UV (C2H5OH) lambdamax=226 (epsilon = 11821), 263 (epsilon = 725), 274 (epsilon = 439); Anal. Calcd. for C19H21N1O5S: C,60.78; H,5.64; N,3.73; S, 8.54. Found: C, 60.57; H, 5.69; N, 3.52; S, 8.56; 1H NMR (300 MHz,CDCl3) delta 1.96-2.13 (m, 2H); 2.42 (s, 3H); 3.43-3.62 (m, 4H); 5.05 (s, 1H); 5.10 (s, 2H); 7.33 (s, 7H); 7.77 (d, j=7.9Hz, 2H).
 

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