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Chemical Structure| 903555-99-7 Chemical Structure| 903555-99-7
Chemical Structure| 903555-99-7

(R)-tert-Butyl (5-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

CAS No.: 903555-99-7

4.5 *For Research Use Only !

Cat. No.: A392773 Purity: 97%

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Product Details of [ 903555-99-7 ]

CAS No. :903555-99-7
Formula : C15H18N2O2
M.W : 258.32
SMILES Code : O=C(OC(C)(C)C)N[C@@H]1CCC2=C1C=CC(C#N)=C2
MDL No. :MFCD29058913
InChI Key :MGRQZBYHVQSEQQ-CYBMUJFWSA-N
Pubchem ID :118990136

Safety of [ 903555-99-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H315-H319-H332-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 903555-99-7 ]

* 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 [ 903555-99-7 ]

[ 903555-99-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 903555-98-6 ]
  • [ 557-21-1 ]
  • [ 903555-99-7 ]
YieldReaction ConditionsOperation in experiment
47% tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 110℃; for 18h; A mixture of <strong>[903555-98-6](5-bromo-indan-1-yl)-carbamic acid tert-butyl ester</strong> (460 mg), Pd(PPh3)4 (89 mg), Zn(CN)2 (200 mg), and DMF (5 mL) under an atmosphere of Ar in a sealed vial was allowed to stir at 110 C. for 18 h. The mixture was allowed to cool to 22 C., Et2O (20 mL) and water (20 mL) were added. The aqueous layer was washed four times with Et2O (10 mL). The combined organic layers were washed three times with water (10 mL), once with brine (10 mL), dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography (4:1 hexanes: ethyl acetate, Rf=0.2) to afford a clear oil (170 mg; 47%). [MH]+=259.
  • 2
  • [ 903555-98-6 ]
  • potassiumhexacyanoferrate(II) trihydrate [ No CAS ]
  • [ 903555-99-7 ]
YieldReaction ConditionsOperation in experiment
94% With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos; In 1,4-dioxane; water; at 105℃; for 5h; To a solution of <strong>[903555-98-6]tert-butyl N-[(1R)-5-bromo-2,3-dihydro-1H-inden-1-yl]carbamate</strong> (25.5 g, 81.7 mmol, 1.00 equiv) in dioxane (270 mL) were added K4Fe(CN)6.3H2O (17.3 g, 41 mmol, 0.50 equiv), 2nd Generation XPhos precatalyst (965 mg, 1.23 mmol, 0.02 equiv), X-phos (584 mg, 1.22 mmol, 0.01 equiv), and a solution of KOAc (16.0 g, 163 mmol, 2.00 equiv) in water (270 mL) under nitrogen. After stirring at 105 oC for 5 h, the resulting solution was diluted with EA (500 mL). The solids were removed by filtration. The filtrate was separated and the aqueous layer was extracted with EA (300 mL) twice. The combined organic layers were washed with brine (300 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EA/PE, 15/85) to give 20 g (94%) of tert-butyl N-[(1R)-5-cyano-2,3-dihydro-1H-inden-1- yl]carbamate as a white solid. LRMS (ES) m/z 259 (M+H).
 

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