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Structure of 317358-61-5

Chemical Structure| 317358-61-5

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Product Details of [ 317358-61-5 ]

CAS No. :317358-61-5
Formula : C13H18BrNO2
M.W : 300.19
SMILES Code : O=C(OC(C)(C)C)N(CC1=CC=CC(Br)=C1)C
MDL No. :MFCD09701230
InChI Key :DJNHISMHPSMPBN-UHFFFAOYSA-N
Pubchem ID :20738487

Safety of [ 317358-61-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 317358-61-5 ]

* 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 [ 317358-61-5 ]

[ 317358-61-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 171663-13-1 ]
  • [ 74-88-4 ]
  • [ 317358-61-5 ]
YieldReaction ConditionsOperation in experiment
100% b-tert-Butyl (3-bromobenzyl)methylcarbamate5.4 g (134 mmol) of 60% sodium hydride are added to a solution of 32 g (111 mmol) of <strong>[171663-13-1]tert-butyl (3-bromobenzyl)carbamate</strong> in 450 mL of dimethylformamide. The reaction medium is stirred at room temperature for 30 minutes and 21 mL (335 mmol) of iodomethane are then added. The reaction medium is stirred at room temperature for 20 hours and then hydrolyzed in water and extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent is evaporated off and 36.2 g (100%) of tert-butyl (3-bromobenzyl)methylcarbamate are obtained in the form of an orange-colored oil.
100% 5.4 g (0.134 mol, 1.2 eq.) of 60% sodium hydride are added to a solution of 32.0 g (0.111 mol, 1 eq.) of <strong>[171663-13-1]tert-butyl (3-bromobenzyl)carbamate</strong> in 450 ml of dimethylformamide. The reaction medium is stirred at ambient temperature for 30 minutes and then 20.9 ml (0.335 mol, 3 eq.) of iodomethane are added. The reaction medium is stirred at ambient temperature for 20 hours, then hydrolysed in water and extracted with ethyl acetate. The organic phases are combined, washed with a saturated sodium chloride solution and dried over sodium sulphate. The solvent is evaporated and 36.23 g of tert-butyl (3-bromobenzyl)(methyl)carbamate are obtained in the form of an orange oil. Yield = 100%
92% With sodium hydride; In DMF (N,N-dimethyl-formamide); 19 g (475 mmol) of sodium hydride (60% in oil) are added portionwise to a solution of 128 g (447 mmol) of tert-butyl (3-bromobenzyl) carbamate in 800 ml of DMF, and the reaction medium is stirred until the evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out by settling of the phases, dried over magnesium sulphate and evaporated. 152.5 g of ter-butyl (3-bromobenzyl) -N-methylcarbamate are obtained in a yield of 92%
In N,N-dimethyl-formamide; (b) tert-butyl (3-bromobenzyl)-N-methylcarbamate 128 g (447 mmol) of <strong>[171663-13-1]tert-butyl (3-bromobenzyl)carbamate</strong> and 800 ml of DMF are introduced into a round-bottomed flask and under a nitrogen stream. 19 g (475 mmol) of sodium hydride (60% in oil) are added in small quantities and the mixture is stirred until the gas emission ceases. 29.3 ml (470 mmol) of methyl iodide are then added and the mixture is stirred overnight. The reaction medium is poured into ice-cold water, extracted with ethyl acetate, the organic phase decanted off, dried over magnesium sulphate and evaporated off. 152.5 g (92%) of the expected product are recovered.

  • 2
  • [ 171663-13-1 ]
  • [ 317358-61-5 ]
YieldReaction ConditionsOperation in experiment
(b) tert-Butyl (3-bromo benzyl)-N-methylcarbamate In a manner similar to that of Example 1(b), starting with 85 g (297 mmol) of tert-butyl (3-bromo benzyl)carbamate, 92.5 g (100%) of the expected product are obtained.
  • 3
  • [ 568577-88-8 ]
  • [ 317358-61-5 ]
  • tert-butyl methyl[4'-(morpholin-4-yl)biphenyl-3-yl]methyl}carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 90℃; for 36h; To a mixture of tert-butyl (3-bromobenzyl)methylcarbamate (14; 2.10 g, 7.00 mmol) in DME (21 mL)/water(11 mL) were added <strong>[568577-88-8]4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine</strong> (15; 2.12 g, 7.35 mmol), Pd(PPh3)4 (243 mg, 0.21 mmol) and Na2CO3 (2.22 g, 21.0 mmol). The mixture was stirred at 90 C for 36 h. After being cooled to room temperature, the mixture was concentrated in vacuo. The residue was diluted with water and extracted with CHCl3. The organic layer was dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (CHCl3/MeOH = 98/2) to afford tert-butyl methyl[4'-(morpholin-4-yl)biphenyl-3-yl]methyl}carbamate (2.20 g, 82%) as a colorless oil. To a solution of tert-butyl methyl[4'-(morpholin-4-yl)biphenyl-3-yl]methyl}carbamate (1.82 g, 4.76 mmol) in EtOH (20 mL) was added 4 M HCl/EtOAc (10.0 mL, 40.0 mmol). After being stirred at room temperature for 24 h, the mixture was concentrated in vacuo. The residue was diluted with saturated NaHCO3 aqueous solution, and the mixture was extracted with CHCl3. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the product (1.24 g, 92%).
 

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