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Chemical Structure| 405239-72-7 Chemical Structure| 405239-72-7

Structure of 405239-72-7

Chemical Structure| 405239-72-7

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Product Details of [ 405239-72-7 ]

CAS No. :405239-72-7
Formula : C16H22N2O4
M.W : 306.36
SMILES Code : O=C(N1CC(C(N(OC)C)=O)CCC1)OCC2=CC=CC=C2
MDL No. :MFCD09756513

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Application In Synthesis of [ 405239-72-7 ]

* 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 [ 405239-72-7 ]

[ 405239-72-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 27550-90-9 ]
  • isobutyl chioroformate [ No CAS ]
  • [ 6638-79-5 ]
  • [ 78190-11-1 ]
  • [ 405239-72-7 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; To a cooled (-15 C. to -20 C.) and stirred solution of <strong>[78190-11-1]1-[(benzyloxy)carbonyl]-3-piperidinecarboxylic acid</strong> (4.0 g, 15.2 mmol) in dry THF (50 mL) including methylmorpholine (2 mL) was added dropwise a solution of isobutyl chioroformate (2.28 g, 16.7 mmol) in THF (10 mL). After the mixture was stirred at the same temperature for 20 min, a solution of N,O-dimethylhydroxylamine hydrochloride (1.63 g, 16.7 mmol) in THF (20 mL) including methylmorpholine (2 mL) was added. The reaction mixture was allowed to warm to room temperature, and then stirred for 16 hrs. The reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The separated organic phase was washed with 1N HCl, saturated NaHCO3, and brine, successively. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to give benzyl 3-[methoxy(methyl)amino]carbonyl)-1-piperidinecarboxylate as a colorless oil (4.7 g, yield; quant.).
  • 2
  • [ 6638-79-5 ]
  • [ 78190-11-1 ]
  • [ 405239-72-7 ]
YieldReaction ConditionsOperation in experiment
93% To a solution of 1-benzyloxycarbonylpiperidinc-3-carboxylic acid (10 g, 43.6 mmol) in THF(100 mL) at 0 C was addcd 1,V-carbonyldiimidazole (38.57 g, 52.3 mmol). The mixture wasstirred at 0 C for 1 h. Triethylamine (7.13 g, 69.8 mmol) was added followed by Nmethoxymethanamine hydrochloride (6.38 g, 65.4 mmol). The mixture was allowed to warm to room temperature and stirred for 16 h. The mixture was diluted with EtOAc, washed with 0.5 N HC1, sat. NaHCO3, and brine. The organic layer was dried (Na2SO4), filtered and concentrated. The crude product was purified by silica flash chromatography (0-30% EtOAc/heptane) to givethe title compound (11.03 g, 93% yield) as a colorless oil. ?H NMR (400 MHz, Chloroform-d)7.40 -7.28 (m, 5H), 5.20-5.07 (m, 211), 4.15 (d,J 34.48 Hz, 2H), 3.66 (ci, Jr 38.49 Hz, 3H),3.16 (s, 3H), 2.94 (d,J= 12.21 Hz, 111), 1.99- 1,88 (m, 111), 1.79-1.62 (m, 2H), 1.57 (s, 211).LCMS (EST) mz 307.2 [M+Hj.
83% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 2 - 20℃; Step 2. Benzyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; A 1000-mL 3-necked round-bottom flask was charged with a solution of N-methoxymethan amine hydrochloride (21.45 g, 217.7 mmol, 1.10 equiv, 99%) in dichloromethane (DCM) (250 mL). To the mixture was added Et3N (22.22 g, 217.80 mmol, 1.10 equiv, 99%) at 0-10 C., followed by addition <strong>[78190-11-1]1-(benzyloxycarbonyl)piperidine-3-carboxylic acid</strong> (58 g, 220.3 mmol, 1.00 equiv) in dichloromethane (150 mL) drop wise at 2 C. over 2 hr period. To this mixture was added EDC.HCl (42.02 g, 217.80 mmol, 1.10 equiv, 99%) in several batches while maintaining the temperature below 5 C. The resulting solution was allowed to stir at room temperature overnight. The progress was monitored by TLC (EtOAc: PE=1:1). Upon completion, the reaction was then quenched by the addition of water (500 mL). The resulting mixture was then extracted with dichloromethane (2×500 mL). Combined organic layers were dried over anhydrous magnesium sulfate and concentrated on a rotary evaporator. The resulting residue was purified by a silica gel column chromatography eluted with ethyl acetate/petroleum ether (1:10) affording benzyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate as a white syrup (57 g, 83%).
 

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