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Chemical Structure| 86661-32-7 Chemical Structure| 86661-32-7

Structure of 86661-32-7

Chemical Structure| 86661-32-7

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Product Details of [ 86661-32-7 ]

CAS No. :86661-32-7
Formula : C17H25NO5S
M.W : 355.45
SMILES Code : O=C(N1[C@H](COS(=O)(C2=CC=C(C)C=C2)=O)CCC1)OC(C)(C)C
MDL No. :MFCD11505918

Safety of [ 86661-32-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 86661-32-7 ]

* 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 [ 86661-32-7 ]

[ 86661-32-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 151-50-8 ]
  • [ 86661-32-7 ]
  • [ 142253-50-7 ]
YieldReaction ConditionsOperation in experiment
66% In dimethyl sulfoxide; at 90.0℃; for 6.5h; c) _VBOC-(2>S)-2-Cyano-1-pyrrolidine. A mixture of -N-13OC-(2?)-2-([(4-methylphenyl)snlfonyl]oxy}methyl)-1-pyrrohdine (460 mg, 1 29mmol) and KCN (256 mg, 3.88 mmol) wore boated at 90 "C in DMSO (10 niL) for 6.5 h.The mixture was cooled to room temperature and IUtOAc and water were added. Theorganics were washed with water twice and then with brine. The aqueous layerswere extracted with EtOAc and the combined organics dried over NasSO*), filtered andconcentrated followed by flash chromatography purification to give ./V-BOC-(2S)-2-cyano-1-pyrrolidine (179 mg, 66%) as an oil. 1H NMR exists as rotomers(CDCl3) delta 3.99 (m, 1 H), 3.43-3.37 (m, 2 H), 2.83-2 51 (m, 2 H), 2.17-1.83 (m, 4 H), 1.46and 1,44 (s, 9 H rotomeric BOC £- butyl).
  • 2
  • potassium cyanide [ No CAS ]
  • [ 86661-32-7 ]
  • [ 142253-50-7 ]
YieldReaction ConditionsOperation in experiment
57.5% In dimethyl sulfoxide; at 110.0℃; for 3h; Step c 2S-Cyanomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester. The product of step b (4.3 g, 12.1 mmol) and potassium cyanide (1.6 g, 24.2 mmol) were heated together in dimethyl sulfoxide at 110C for 3h. The reaction mixture was cooled to ambient temperature and poured into water (200 ml). The product was extracted with ethyl acetate (3x50 ml), the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate 70:30) to afford the the title compound as a colourless oil (1.46 g, 57.5%). 1H NMR 4.00 (1H, br s), 3.41 (2H,m), 2.74 (2H, m), 2.16 (1H, m), 1.92 (3H, m), 1.47 (9H, s).
  • 3
  • [ 773837-37-9 ]
  • [ 86661-32-7 ]
  • [ 142253-50-7 ]
YieldReaction ConditionsOperation in experiment
66% In dimethyl sulfoxide; at 100.0℃; for 4h; Intermediate 5(S)-tert-Butyl 2-(cyanomethyl)pyrrolidine- 1 -carboxy late[0231][Chemical Formula 36]To a solution of intermediate 6 (90.4 g, 255 mmol) in dimethylsulfoxide (255 mL) was added sodium cyanide (16.2 g, 331 mmol), and heated to 100C. After stirring for 4 hours, to the mixture was added water, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified with silica gel column (hexane/ethyl acetate = 70/30 to 30/70) to give the title compound (35.2 g, 168 mmol, 66%).MS (ESI+) 211 (M++l, 100%)
Intermediate 139: ferf-Butyl (S)-2-cyanomethylpyrrolidine-l-carboxylate[00485] Sodium cyanide (8.2g) was added to a solution of ferf-butyl (S)-2-(4- methylbenzenesulfonyloxymethyl)pyrrolidine-l-carboxylate (Intermediate 140, 29.6g) in DMSO (300mL) and the resultant mixture was stirred and heated at 90C for 5.5 hours. After cooling, the mixture was treated with saturated aqueous iron (II) sulphate solution and the mixture was stirred for a further 5 hours then extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SC>4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether (5%) to give ferf-butyl (S)-2-cyanomethylpyrrolidine-l-carboxylate (13.0g) as a light yellow oil which was used without further characterisation.
13.0 g Intermediate 139: tert-Butyl (S)-2-cyanometh lpyrrolidine- 1 -carboxylate [00410] Sodium cyanide (8.2g) was added to a solution of tert-butyl (S)-2-(4- methylbenzenesulfonyloxymethyl)pyrrolidine-l -carboxylate (Intermediate 140, 29.6g) in DMSO (300mL) and the resultant mixture was stirred and heated at 90C for 5.5 hours. After cooling, the mixture was treated with saturated aqueous iron (II) sulphate solution and the mixture was stirred for a further 5 hours then extracted with ethyl acetate. The organic layer was washed with brine, dried ( a2S04) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether (5%) to give tert-butyl (S)-2-cyanomethylpyrrolidine- 1 -carboxylate (13.0g) as a light yellow oil which was used without further characterisation.
1.77 g In dimethyl sulfoxide; at 90.0℃;Inert atmosphere; Step 2: (S)-tert-butyl 2-(cyanomethyl)pyrrolidine-l-carboxylate [00277] To a solution of (S)-tert-butyl 2-(tosyloxymethyl)pyrrolidine-l-carboxylate (4.2 g) in DMSO (36 mL) was added sodium cyanide (0.97 g, 19.9 mmol). The reaction mixture was stirred at 90C under argon overnight. After cooled to room temperature, the reaction mixture was treated with saturated FeS04 solution (50 mL) at room temperature for another 5 hours and then extracted with EtOAc (50 mL x 3). The combined organic extracts were washed with saturated NaCl solution (30 mL) and dried over Na2S04. Silica-gel chromatography with 25% EtOAc/Hexane gave the desired product (1.77 g, 84.7% overall yield for steps 1 & 2) as a colorless oil.

 

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