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[ CAS No. 5291-77-0 ]

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Chemical Structure| 5291-77-0
Chemical Structure| 5291-77-0
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Product Details of [ 5291-77-0 ]

CAS No. :5291-77-0 MDL No. :MFCD00003195
Formula : C11H13NO Boiling Point : 343°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :175.23 g/mol Pubchem ID :79176
Synonyms :

Safety of [ 5291-77-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5291-77-0 ]

  • Downstream synthetic route of [ 5291-77-0 ]

[ 5291-77-0 ] Synthesis Path-Downstream   1~16

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YieldReaction ConditionsOperation in experiment
General procedure: To a suspension of NaH(0.80 g, 20.0 mmol, 1.0 eq) in THF (40 mL) at 0 C was added pyrrolidone(1.70 g, 20 mmol, 1.0 eq) and the reaction mixture stirredtherein for 30 min. The reaction was then warmed to r.t. and left tostir for a further 30 min until H2 ceased to evolve. Benzyl bromide(20 mmol, 1.0 eq) was added dropwise and the reaction stirred for12 h. The reaction was quenched by the addition of H2O (500 mL)and extracted with CH2Cl2 (3 x 30 mL). The combined organicextracts were dried and concentrated in vacuo to give desiredproduct. 4.2.7.2. 1-Benzylpyrrolidin-2-one (11a) [75]. Yellow oil; 1H NMR(500 MHz, CDCl3) deltaH (ppm): 7.23-7.36 (m, 5H), 4.45 (s, 2H),3.25-3.29 (m, 2H), 2.42-2.48 (m, 2H), 1.95-2.02 (m, 2H); 13C NMR(125 MHz, CDCl3) deltaC (ppm): 175.0, 136.5, 128.6, 128.1, 127.5, 46.3,45.9, 30.9, 17.7; ESI-MS: m/z 176.1 ([M+H]+).
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YieldReaction ConditionsOperation in experiment
82% To a cold -78 C. solution of 1-benzyl-2-pyrrolidinone (0.422 g, 2.4 mmol, 1.0 equiv.) in anhydrous tetrahydrofuran (15 mL) was added lithium diisopropylamide (2.4 mL of a 2 M solution, 4.8 mmol, 2.0 equiv.) and the resultant red solution was stirred for 30 mins at -78 C., and iodomethane (0.6 mL, 9.6 mmol, 4.0 equiv.) was added. The solution was stirred at -78 C. for 1 hr and allowed to slowly warm to room temperature for 16 hrs. Saturated aqueous ammonium chloride was added and the mixture extracted with ethyl acetate. The organic fraction was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography, eluting with a gradient of 35-80% ethyl acetate in hexanes to afford the product as a tan liquid (0.374 g, 82%). 1H NMR (300 MHz, CDCl3): delta 7.37-7.34 (m, 5H), 4.52-4.41 and 4.46-4.41 (ABq, 2H, J=14.6 Hz), 3.27-3.15 (m, 2H), 2.60-2.46 (m, 1H), 2.28-2.15 (m, 1H), 1.68-1.58 (m, 1H), 1.28-1.25 (d, 3H, J=7.2 Hz).
82% General procedure: To a cold -78 C solution of1-benzyl-2-pyrrolidinone (0.422 g, 2.4 mmol, 1.0 equiv.)in anhydrous tetrahydrofuran (15 mL) was addedlithium diisopropylamide (2.4 mL of a 2 M solution, 4.8 mmol, 2.0 equiv.)and the resultant red solution was stirred for 30 mins at -78 C,andiodomethane (0.6 mL, 9.6 mmol, 4.0 equiv.)was added. The solution was stirred at -78 C for 1 hr and allowed to slowly warm to room temperature for 16 hrs. Saturated aqueous ammonium chloride was added and the mixture extracted with ethyl acetate. The organic fraction was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentratedin vacuo.The crude product was purified by silica gel column chromatography, eluting with a gradient of 35-80% ethyl acetate in hexanes to afford the product as a tan liquid(0.374 g,82%).1H NMR (300 MHz, CDCl3): delta 7.37-7.34 (m, 5H), 4.52-4.41 and 4.46-4.41 (ABq, 2H,J= 14.6 Hz), 3.27-3.15 (m, 2H), 2.60-2.46 (m, 1H), 2.28-2.15 (m, 1H), 1.68-1.58 (m, 1H), 1.28-1.25 (d, 3H,J= 7.2 Hz).
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YieldReaction ConditionsOperation in experiment
With Lawessons reagent; In dichloromethane; at 20℃;Inert atmosphere; General procedure: Lawesson?s reagent (2.02 g, 5.0 mmol) was added to a solution of the lactam (10 mmol) in dry CH2Cl2 (100 mL). The mixture was stirred at room temperature for 1-4 h until the starting material was consumed (TLC monitoring). The solvent was evaporated and the crude mixture was filtered on short column of silica gel (cyclohexane/EtOAc). The thiolactam (10 mmol) was suspended in dry THF (100 mL) and MeI (1.0 mL, 16 mmol) was added. The mixture was stirred at room temperature overnight. The thioiminium ion was isolated by filtration and washed with cold THF to obtain yellowish solid.
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YieldReaction ConditionsOperation in experiment
General procedure: 1-benzylpyrrolidin-2-one (4.63 g, 26.46 mmol) and dimethylsulfate (2.60 mL, 27.40 mmol) were heated at 80 C for 15 h under nitrogen atmosphere. The reaction mixture was then cooled at 50/60 C and a solution of sodium ethoxide (0.742 g of sodium in ethanol (14.0 mL) was added dropwise. The resulting mixture was stirred under nitrogen for 4h at 50/60C. Then nitromethane dried over CaCl2 (3 mL, 55.0 mmol), was added and the resulting solution was refluxed for 10 min. After cooling, the solvent was evaporated under reduced pressure. The residue was dissolved in CH2Cl2, filtered and the solvent evaporated in vacuo.. The resulting oil was purified by column chromatography on silica gel (CH2Cl2/AcOEt, 99/1). Further crystallization from CH2Cl2/petroleum ether afforded compound 2a as white crystals (0.424 g, 28%).
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