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Chemical Structure| 186466-64-8

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Product Details of [ 186466-64-8 ]

CAS No. :186466-64-8
Formula : C10H21NO3
M.W : 203.28
SMILES Code : O=C(OC(C)(C)C)N[C@@H](C(C)(O)C)C
MDL No. :MFCD18831421
InChI Key :ZBSFLGNSQZRBCS-SSDOTTSWSA-N
Pubchem ID :10655774

Safety of [ 186466-64-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 186466-64-8 ]

* 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 [ 186466-64-8 ]

[ 186466-64-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 75-16-1 ]
  • [ 91103-47-8 ]
  • [ 186466-64-8 ]
YieldReaction ConditionsOperation in experiment
100% Intermediate 2-((( 1 R)-2-fluoro- 1 ,2-dimethylpropyl)amino)pyrrolo [ 1 ,2-b]pyridazine-3 -carboxamide [00195] To a solution of <strong>[91103-47-8](R)-methyl 2-(tert-butoxycarbonylamino)propanoate</strong> (10 g, 49.2 mmol) in THF (80 mL) at 0 C was added methyl magnesium bromide (65.6 mL, 197 mmol) dropwise. The reaction mixture was warmed up to RT and stirred for 16 hrs. The reaction mixture was poured into 200 mL of ice water. The mixture was extracted with ethyl acetate (100 mL x 3). The combined organic phases were concentrated to yield a crude product to which was added 100 mL of diethyl ether. Filtration and concentration yielded the title compound (lOg, 100%). 1H-NMR (400 MHz, CDC13) delta ppm 3.60 (1 H, ddd, J=14.5, 7.1, 6.8 Hz), 1.46 (9 H, s), 1.24 (3 H, s), 1.18 (3 H, s), 1.14 (3 H, d, J=7.0 Hz).
99% Example 32.Step 1To a solution of Boc-D-alanine methyl ester (5.00 g, 24.6 mmol) in THF (100 mL) at 0 C was slowly added methyl magnesium bromide (3.0 M in Et20, 28.7 mL, 86.1 mmol). The resultant white slurry was stirred at 0 C for 1 h then at room temperature for 2 h. The reaction mixture was quenched with saturated aqueous NH4C1, diluted with H20 and extracted with EtOAc. The combined organics were washed with brine, dried over MgS04 and concentrated to give 4.93 g (99%) ((R)-2-hydroxy-l,2-dimethyl -propyl)-carbamic acid tert-butyl ester as a colorless viscous oil.
0.86 g In diethyl ether; at 0 - 20℃; for 3h;Inert atmosphere; Step (i): Preparation of tert-butyl [(2R)-3-hydroxy-3-methylbutan-2-yl]carbamate (Compound 228b) Under a nitrogen atmosphere, 3 mol/L methylmagnesium bromide/diethyl ether (5.90 mL) was added to a solution of Boc-D-alanine methyl ester (1.0 g) in diethyl ether (25 mL) at 0 C., and the mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with aqueous ammonium chloride and then extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. The concentrated residue was purified by silica gel column chromatography (eluate: hexane/ethyl acetate=70/30) to give Compound 228b (0.86 g).
0.86 g In diethyl ether; at 0 - 20℃; for 3h;Inert atmosphere; Under a nitrogen atmosphere, a solution of Boc-D-alanine methyl ester (1.0 g) in diethyl ether (25 ml)A 3 mol / L methyl magnesium bromide-diethyl ether solution (5.90 ml) was added at 0 C.,And the mixture was stirred at room temperature for 3 hours.After quenching with ammonium chloride solution,The mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous sodium sulfate.The residue obtained by concentration was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 70/30) to prepare compound 228b (0.86 g).

  • 2
  • [ 91103-47-8 ]
  • [ 74-88-4 ]
  • [ 186466-64-8 ]
  • 3
  • [ 91103-47-8 ]
  • [ 186466-64-8 ]
YieldReaction ConditionsOperation in experiment
99% With methylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 0 - 20℃; for 3h; Example 12.2-(6-Chloro-l-methyl-lH-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2- hydroxy- 1 ,2-dimethyl-propyl)-amideStep 1((R)-2 -Hydro xy-1 ,2-dimeth l-propyl)-carbamic acid tert-butyl esterTo a solution of Boc-D-alanine methyl ester (5.00 g, 24.6 mmol) in THF (100 mL) at 0 C was slowly added methyl magnesium bromide (3.0 M in Et20, 28.7 mL, 86.1 mmol). The resultant white slurry was stirred at 0 C for 1 h then at room temperature for 2 h. The reaction mixture was quenched with saturated aqueous NH4C1, diluted with H20 and extracted with EtOAc. The combined organics were washed with brine, dried over MgS04 and concentrated to give 4.93 g (99%) ((R)-2 -hydro xy-l ,2-dimethyl-propyl)-carbamic acid tert-butyl ester as a colorless viscous oil.
  • 4
  • [ 917-54-4 ]
  • [ 91103-47-8 ]
  • [ 186466-64-8 ]
 

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