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[ CAS No. 153248-46-5 ]

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Chemical Structure| 153248-46-5
Chemical Structure| 153248-46-5
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Product Details of [ 153248-46-5 ]

CAS No. :153248-46-5 MDL No. :MFCD09031543
Formula : C10H19NO3 Boiling Point : 311.3±15.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :201.26 g/mol Pubchem ID :11701224
Synonyms :

Safety of [ 153248-46-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153248-46-5 ]

  • Downstream synthetic route of [ 153248-46-5 ]

[ 153248-46-5 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 24424-99-5 ]
  • [ 45434-02-4 ]
  • [ 153248-46-5 ]
YieldReaction ConditionsOperation in experiment
Step 2: Synthesis of tert-butyl [l-(hydroxymethyl)cyclopropyl]methyl}carbamate Di-tert-butyl dicarbonate (40.5 mL, 197 mmol) is added to a stirred solution of [1- (aminomethyl)cyclopropyl]methanol (20 g, 198 mmol) in CH2C12 (600 mL) at room temperature. The reaction mixture is stirred at same temperature for 40 h. Then saturated NH4C1 solution (250 mL) is added and the reaction mixture is stirred for another 10 min. The organic layer is separated, washed with saturated NaHC03 solution (100 mL), dried (Na2S04) and concentrated to afford the title compound (20 g, 56 % for 2 steps) as a white solid.
  • 2
  • [ 153248-46-5 ]
  • [ 124-63-0 ]
  • methanesulfonic acid 1-(<i>tert</i>-butoxycarbonylamino-methyl)-cyclopropylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 3h; To a mixture of23b (100 mg, 0.5 mmol, 1.0 equiv) and methanesulfonyl chloride(60 mg, 0.525 mmol,1.05 equiv) in dry DCM (2 mL), was added Et3N(61 mg, 0.6 mmol, 1.2 equiv). The reaction was stirred at roomtemperature for 3 h, and then ethyl acetate and water were added.The organic phase was washed with water and brine, dried overanhydrous Na2SO4, filtered and concentrated. The resulting residue24b was employed for use without further purification.
  • 3
  • [ 153248-46-5 ]
  • [ 877204-21-2 ]
  • 4
  • [ 153248-46-5 ]
  • [ 877204-20-1 ]
  • 5
  • [ 153248-46-5 ]
  • 1-((1-((1H-imidazol-1-yl)methyl)cyclopropyl)methyl)-3-(3,4-dimethoxy-phenyl)thiourea [ No CAS ]
  • 6
  • [ 6914-80-3 ]
  • [ 153248-46-5 ]
  • 8
  • [ 204376-48-7 ]
  • [ 153248-46-5 ]
YieldReaction ConditionsOperation in experiment
Under an argon atmosphere l-(tert-Butoxycarbonylamino-methyl)- cyclopropanecarboxylic acid (3.23g, 15.0 mmol) was dissolved in THF (50 ml_) and cooled to -70 C. Borane tetrahydrofurane complex (1 M in THF, 22.5 mL, 22,5 mmol) was added at -70 C. The mixture was then stirred at 0 C for 2,5h after which borane tetrahydrofurane complex (1 M in THF, 7.5 mL, 7.5 mmol) was added at 0 C. The mixture was stirred at RT for 1.5 h. Aq. NH4CI (50 mL) was added at 20 C and the aqueous phase was extracted with EtOAc (x3). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo to afford (l-Hydroxymethyl-cyclopropylmethyl)-carbamic acid tert-butyl ester (2.6g) as an oil.
  • 9
  • [ 153248-46-5 ]
  • [ 153248-47-6 ]
YieldReaction ConditionsOperation in experiment
Under an argon atmosphere oxalyl chloride (1.17 mL, 13.8 mmol) was dissolved in DCM (30 mL) and cooled to -70 C. DMSO (1.95 mL, 27.6 mmol) in DCM (2.5 mL) was added over 5 min and stirred for 10 min. (1-Hydroxymethyl- cyclopropylmethyl)-carbamic acid tert-butyl ester (2.6g, 12 mmol) in DCM (8.5 mL) was added at -70 C over 5 min and the mixture was stirred for 30 min. Et3N (6.4 mL, 45.6 mmol) was added over 5 min and the temperature was allowed to reach RT over 1 h. H2O was added and the aqueous phase was extracted with DCM (x 2). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica using heptane : EtOAc 1 : 15 as eluent to afford (l-Formyl-cyclopropylmethyl)-carbamic acid tert-butyl ester (0.65g)as an oil.
With pyridinium chlorochromate; In dichloromethane; at 25℃; for 2h; To a solution of tert-butyl ((1 -(hydroxymethyl)cyclopropyl)methyl)carbamate (1 equiv.) in dichloromethane at 25 C was added PCC (1.15 equiv.) in a single portion. Reaction was stirred for 2 h. Diethyl ether was added to the vessel, and the heterogeneous mixture was filtered through silica gel to yield the desired aldehyde intermediate, which was used without further purification.
  • 10
  • [ 153248-46-5 ]
  • [ 107516-75-6 ]
  • [ 1311369-22-8 ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 60h; Step 3: Synthesis of diethyl l-[(l-[(tert- butoxycarbonyl)amino]methyl}cyclopropyl)methyl]-1H-indole-2,6-dicarboxylateTo a solution of tert-butyl { [l-(hydroxymethyl)cyclopropyl]methyl}carbamate (20 g, 99.5 mmol), <strong>[107516-75-6]diethyl 1H-indole-2,6-dicarboxylate</strong> (26 g, 99.5 mmol) and triphenylphosphine (52 g, 199 mmol) in THF (300 mL) is added diisopropyl azodicarboxylate (31 mL, 199 mmol) at room temperature. The reaction mixture is stirred for 60 h and the solvent is evaporated. The residue is purified by flash column chromatography using 12% EtOAc in petroleum ether to afford a mixture of diethyl 1- [(l-{ [(tert-butoxycarbonyl)amino]methyl}cyclopropyl)methyl]-1H-indole-2,6- dicarboxylate and <strong>[107516-75-6]diethyl 1H-indole-2,6-dicarboxylate</strong> (36 g) as a white solid. The mixture is used in the next step without further purification.
  • 14
  • [ 3697-69-6 ]
  • [ 153248-46-5 ]
  • 15
  • [ 220145-17-5 ]
  • [ 153248-46-5 ]
YieldReaction ConditionsOperation in experiment
88% In tetrahydrofuran; at 0 - 23℃; for 4h; Methyl 1 -((Qert-butoxycarbonyl)amino)methyl)cyclopropanecarboxylate (1 equiv.) was dissolved in THF and cooled to 0 C. Lithium aluminum hydride (3 equiv.) was added slowly to the vessel, and contents were stirred while allowing warming up to 23 C over a period of 4 h. The reaction solution was then re-cooled to 0 C, then water (x mL of water/x g of LiA1H4 used), 15% sodium hydroxide solution (x mL of water/x g of LiA1H4 used), and water (3x mL of water/x g of LiA1H4 used) were slowly added to the reaction in a sequential manner. The reaction was filtered through celite, and the filtrate was concentrated in vacuo. The residue was purified via silica gel chromatography to deliver the desired alcohol intermediate, tert-butyl ((1-(hydroxymethyl)cyclopropyl)methyl)carbamate (0.41 g, 88 % yield).
  • 16
  • [ 153248-46-5 ]
  • 5-amino-3-(1,2,3,4-tetrahydronaphthalen-2-yl)-1H-pyrazole-4-carbonitrile [ No CAS ]
  • tert-butyl ((1-((5-amino-4-cyano-3-(1,2,3,4-tetrahydronaphthalen-2-yl)-1H-pyrazol-1-yl)methyl)cyclopropyl)methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
400 mg To a solution of tert-butyl (1- (hydroxymethyl) cyclopropyl) methylcarbamate (200 mg, 1.01 mmol) in DCM (10 ml) was added TEA (0.3 ml, 2.0 mmol) and MsCl (126 mg, 1.1 mmol) at 0 for 1h. 10 ml of NaHCO3was added and extracted with EA (10 ml) , dried over Na2SO4, evaporated in vacuum to give a colorless oil which was used directly in the next step. The crude product was dissolved in DMF (5 ml) and 5-amino-3- (1, 2, 3, 4-tetrahydronaphthalen-2-yl) -1H-pyrazole-4-carbonitrile (190 mg, 0.8 mmol) was added at 60 , then the mixture was stirred at 60 for 1h. TLC showed the starting material (SM) was consumed completely. 25 ml of water was added and extracted with EA (20 ml) , combined organic layer was washed with brine (20 ml) , dried over Na2SO4, evaporated under vacuum to give colorless oil (400 mg) , which was purified by prep-TLC (P/E1: 1) to give a white solid (290 mg) . MS (ESI) m/e [M+1] + 422.1H NMR (400 MHz, DMSO-d6) delta 7.11 (m, 4H) , 6.80 (s, 1H) , 6.56 (s, 1H) , 3.87 (s, 2H) , 3.05-2.90 (m, 5H) , 2.84 (dd, J9.1, 5.4 Hz, 2H) , 2.10 (d, J13.9 Hz, 1H) , 1.84 (dd, J12.9, 8.6 Hz, 1H) , 1.37 (m, 9H) , 1.31 (s, 2H) , 0.43 (dd, J23.2, 3.6 Hz, 4H) .
  • 17
  • [ 153248-46-5 ]
  • 5-amino-1-((1-(aminomethyl)cyclopropyl)methyl)-3-(1,2,3,4-tetrahydronaphthalen-2-yl)-1H-pyrazole-4-carboxamide [ No CAS ]
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