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[ CAS No. 1391730-27-0 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 1391730-27-0
Chemical Structure| 1391730-27-0
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Product Details of [ 1391730-27-0 ]

CAS No. :1391730-27-0MDL No. :
Formula : C17H25NO5S Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :355.45Pubchem ID :-
Synonyms :

Computed Properties of [ 1391730-27-0 ]

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

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Application In Synthesis of [ 1391730-27-0 ]

  • Downstream synthetic route of [ 1391730-27-0 ]

[ 1391730-27-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 98-59-9 ]
  • [ 199174-24-8 ]
  • [ 1391730-27-0 ]
YieldReaction ConditionsOperation in experiment
97.5% With triethylamine; In dichloromethane; at 20℃;Inert atmosphere; To a mixture of (S)-tert-butyl 3 -(hydroxymethyl)pyrrolidine- 1 -carboxylate (3.00 g, 14.9 mmol) and TEA (4.52 g, 44.7 mmol) in DCM (30 mL) was added 4-methylbenzene-1- sulfonyl chloride (4.26 g, 22.4 mmol) under N2 atmosphere. The mixture was stirred at room temperature overnight. The mixture was diluted with DCM and washed with a solution of iNHC1 and saturated aqueous lithium chloride solution and brine successively, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 25 : ito 10: 1) to give (S)-tert-butyl 3- (tosyloxymethyl)pyrrolidine-1-carboxylate (5.17g, 97.5% yield) as a colorless oil. LC-MS: m/z = 356 [M+Hj.
With pyridine; A) tert-butyl (3S)-3-((tosyloxy)methyl)pyrrolidine-1-carboxylate To a mixture of <strong>[199174-24-8]tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate</strong> (48.5 g) and pyridine (200 mL) was added 4-methylbenzene-1-sulfonyl chloride (50.5 g) at room temperature, and the mixture was stirred at room temperature overnight. The solvent of the reaction mixture was evaporated under reduced pressure, and the residue was diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (78.4 g). 1H NMR (300 MHz, CDCl3) delta 1.44 (9H, s), 1.63-1.73 (1H, m), 1.95 (1H, brs), 2.40-2.64 (4H, m), 3.00 (1H, dd, J=11.1, 7.0 Hz), 3.21-3.54 (3H, m), 3.87-4.05 (2H, m), 7.36 (2H, d, J=8.3 Hz), 7.79 (2H, d, J=8.3 Hz).
With pyridine; H) tert-butyl (3S)-3-((tosyloxy)methyl)pyrrolidine-1-carboxylate To a mixture of <strong>[199174-24-8]tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate</strong> (48.5 g) and pyridine (200 mL) was added 4-methylbenzene-1-sulfonyl chloride (50.5 g) at room temperature, and the mixture was stirred at room temperature overnight. The solvent of the reaction mixture was evaporated under reduced pressure, and the residue was diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (78.4 g). 1H NMR (300 MHz, CDCl3) delta 1.44 (9H, s), 1.63-1.73 (1H, m), 1.95 (1H, brs), 2.40-2.64 (4H, m), 3.00 (1H, dd, J=11.1, 7.0 Hz), 3.21-3.54 (3H, m), 3.87-4.05 (2H, m), 7.36 (2H, d, J=8.3 Hz), 7.79 (2H, d, J=8.3 Hz).
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