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[ CAS No. 1108172-95-7 ] {[proInfo.proName]}

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Chemical Structure| 1108172-95-7
Chemical Structure| 1108172-95-7
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Product Details of [ 1108172-95-7 ]

CAS No. :1108172-95-7 MDL No. :MFCD31696553
Formula : C11H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 212.29 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1108172-95-7 ]

* 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 [ 1108172-95-7 ]

[ 1108172-95-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1108172-95-7 ]
  • [ 166599-84-4 ]
  • [ 1108172-98-0 ]
YieldReaction ConditionsOperation in experiment
To a solution of the respective carboxylic acid (0.85 mmol) in DMF (4.0 mL) is added successively DIPEA (2.40 mmol) and TBTU (0.97 mmol). The obtained mixture is stirred for 10 min and treated with a solution of (lS,2S,5R)-2-Aminomethyl-3-aza- bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (0.84 mmol) in DMF (1.5 mL). After LC-MS indicated complete conversion (10 min - 16 h) sat. aq. NaHCOs solution and ether (50 mL) are added, the layers are separated and the aq. layer is extracted twice with ether. The combined organic layers are washed twice with sat. NaHCC>3 solution, twice with citric acid (5% in water) and once with brine. After drying over MgSO4 and removal of solvents in vacuo the respective amide is obtained which is either purified by FC (EtO Ac/heptane) or used without further purification.; (lS,2S,5R)-2-[(Benzofuran-4-carbonyl)-amino]-methyl}-3-aza- bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (method A) prepared by reaction of (lS,2S,5R)-2-Aminomethyl-3-aza-bicyclo[3.1.0]hexane- 3-carboxylic acid tert-butyl ester with <strong>[166599-84-4]benzofuran-4-carboxylic acid</strong> (M.A. Eissenstat et al. J. Med. Chem. 1995, 38, 3094-3105). LC-MS (basic): tR = 0.91 min; [M+H]+ = 357.2.
Reference： [1]Patent: WO2009/16560,2009,A2 .Location in patent: Page/Page column 93-94
  • 2
  • [ 1108172-95-7 ]
  • [ 364-74-9 ]
  • tert-butyl (1S,2S,5R)-2-(((4-fluoro-2-nitrophenyl)amino)methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.37% With potassium carbonate; In acetonitrile; at 15 - 82℃; for 2h; To a solution of tert-butyl (1S,2S,5R)-2-(aminomethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (3.7 g) and potassium carbonate in acetonitrile (30 mL) was added 1,4-difluor-2-nitrobenzene (2.77 g, 17.43 mmol, 1.89 mL) at 15 C under N2. The mixture was warmed to 82 C and stirred for 2 h. The mixture was added with water (100 mL) and then extracted with EtOAc (200 mL X 1). The combined organic phase was washed with aq NaCl (100 mL X 1), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography eluted with Pet. Ether/EtOAc (20/1 to 10/1) to give tert-butyl (1S,2S,5R)-2-(((4-fluoro-2-nitrophenyl)amino)methyl)-3-azabicyclo[3.1.0]hexane-3-c arboxylate (5.3 g, 15.05 mmol, 86.37%). 1HNMR (CDCl3, 400 MHz): delta 8.38-8.14 (m, 1H), 7.90 (td, J = 9.76, 2.95 Hz, 1H), 7.14-6.92 (m, 1H), 4.28-4.09 (m, 1H), 3.62-3.34 (m, 4H), 1.65-1.56 (m, 1H), 1.47 (d, J = 14.81 Hz, 10H), 0.82-0.72 (m, 1H), 0.26-0.16 (m, 1H).
Reference： [1]Patent: EP3450430,2019,A1 .Location in patent: Paragraph 0305; 0314

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