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[ CAS No. 220145-17-5 ] {[proInfo.proName]}

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Chemical Structure| 220145-17-5
Chemical Structure| 220145-17-5
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Product Details of [ 220145-17-5 ]

CAS No. :220145-17-5 MDL No. :
Formula : C11H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 229.27 Pubchem ID :-
Synonyms :

Safety of [ 220145-17-5 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 220145-17-5 ]

* 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 [ 220145-17-5 ]

[ 220145-17-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 6914-73-4 ]
  • [ 220145-17-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / Raney-Ni / methanol / 4 h / 750.06 Torr / Ambient temperature 2: 80 percent / Et3N / acetonitrile / 2 h / 0 °C
Reference： [1]Seebach, Dieter; Abele, Stefan; Sifferlen, Thierry; Haenggi, Martin; Gruner, Sibylle; Seiler, Paul [Helvetica Chimica Acta, 1998, vol. 81, # 12, p. 2218 - 2243]
  • 2
  • [ 6914-79-0 ]
  • [ 220145-17-5 ]
Reference： [1]Helvetica Chimica Acta,1998,vol. 81,p. 2218 - 2243
  • 3
  • [ 220145-17-5 ]
  • [ 1170782-90-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In 1,4-dioxane at 25℃; for 5h; 11.a (Trimethylsilyl)diazomethane (4.41 mL of a 1.0 M solution in diethyl ether, 8.82 mmol) was added over 5 min to a solution of racemic 1-(tert-butoxycarbonylamino-methyl)-cyclopropanecarboxylic acid (0.95 g, 4.41 mmol) in a 1:1 mixture of methanol/benzene (30 mL) at 0° C. The resulting yellow solution was stirred at 0° C. for 1 h, and then was concentrated in vacuo. The residue was dissolved in 1,4-dioxane (20 mL) at 25° C. and a 4.0 M solution of hydrochloric acid in 1,4-dioxane (20 mL) was subsequently added. After stirring at 25° C. for 5 h, the reaction mixture was concentrated in vacuo to afford a sticky oil. This material was dissolved in toluene (80 mL) and the solution was concentrated in vacuo (the process was then repeated). The resulting residue was dissolved in methanol (30 mL) at 25° C. and 4-fluorobenzaldehyde (0.473 mL, 4.41 mmol), sodium acetate (0.723 g, 8.81 mmol), powdered/activated 4 molecular sieves (1.87 g) and sodium cyanoborohydride (0.554 g, 8.82 mmol) were added sequentially. The mixture was stirred at 25° C. for 19 h, then was filtered through Celite. The Celite was washed with methanol (2×30 mL) and the combined filtrate and washings were concentrated in vacuo. The residue was partitioned between half-saturated aqueous sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL). The combined organic layers were dried over sodium sulfate and were concentrated in vacuo. The residue was purified by flash column chromatography (Teledyne Isco RediSep column; 50-100% ethyl acetate in hexanes) to afford 1-[(4-fluoro-benzylamino)-methyl]-cyclopropanecarboxylic acid methyl ester (0.050 g, 0.211 mmol, 5%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ: 0.79-0.82 (2H, m), 1.26-1.28 (2H, m), 2.70 (2H, s), 3.66 (3H, s), 3.79 (2H, s), 6.97-7.01 (2H, m), 7.28-7.31 (2H, m).
Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2009/306057, 2009, A1 Location in patent: Page/Page column 60
  • 4
  • [ 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).
Reference： [1]Patent: WO2014/144100,2014,A2 .Location in patent: Paragraph 00274

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