Closed KlementineJBS closed 1 year ago
KBS25-1 RM.d.zip KBS25-1 RM.pdf
Peaks at 155, 193, 231 suggest mixture of mono, bis and tri-propargylated products ([M+H]). Peak at 231 (tri-propargyl) is largest but this may reflect ease of ionisation.
Empty vial: 15.7072 Full vial: 16.1965 Mass: 489.3
KBS-25-1_1-D_6_1_394.d.zip KBS-25-1_1-D_6_1_394-_DataAnalysis__Compound_Spectrum_List_Report.pdf KBS-25-1_1-D_6_1_394ReportEngine-Report.pdf
Began to column crude product (viscous orange liquid). Determined on 20% ethyl acetate in hexanes.
Struggled to dissolve crude product - tried hexane, ethyl acetate/hexane mixture, DCM, chloroform, ether. Was somewhat soluble in chloroform, so put what did dissolve in column and was left with a reddish brown solid remainder (120.6 mg).
F8-11 Empty vial: 15.7919 Full vial: 15.7970 Mass: 5.1 mg
Possibly tris-substituted product.
F18-35 Empty vial: 15.7452 Full vial: 15.9264 Mass: 181.2 mg
Appears to be tetra-substituted product.
KBS25-1 F18-35.pdf 269.26 [M+H]+ (tetra substituted compound)
KBS25-1 insoluble.pdf 269.26 [M+H]+ (tetra substituted compound), 231.27 [M+H]+ (tris substituted compound), 191.13 [M+H]+ (bis substituted compound, desired product)
KBS25-1 insoluble residue.zip KBS25-1 18-35_1.zip KBS25-1 8-11_1.zip
Supports NMR results - insoluble residue (which dissolved easily in MeOH) is a mixture of the three products, while the main product isolated from the column was the undesired tetra-substituted compound.
Link to [HIRAC](), [original method]() and master page.
KBS25 Propargylation of unprotected 1,6-diaminohexane.docx
Reaction Scheme
Attempting to alkylate unprotected amine