pent-4-en-1-amine;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl-1-(3-(4-(allyloxy)phenyl)-3-(ethoxyimino)-propanoylimino)-2-(4-(2-bromoacetamido)-3,5-dichlorophenyl)ethylcarbamate (60 mg) in dichloromethane (0.30 mL) at room temperature was added pent-4-en-1-amine hydrochloride (47 mg) and diisopropylethylamine (76 μL), and the resulting solution was stirred at room temperature for 4 h. The solvents were removed in vacuo to give the title compound as a white solid, which was used in Step B without purification. retention time: 2.10 min (method A). MS (ESI) (M+H)+ 717.83. The solvents were removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl-1-(3-(4-(allyloxy)phenyl)-3-(ethoxyimino)-propanoylimino)-2-(4-(2-bromoacetamido)-3,5-dichlorophenyl)ethylcarbamate (100 mg) in dichloromethane (0.30 mL) at room temperature was added pent-4-en-1-amine hydrochloride (51 mg) and diisopropylethylamine (97 μL), and the resulting solution was stirred at room temperature for 2 h. The solvents were removed in vacuo to give the title compound as a white solid, which was used in Step B without purification. retention time: 2.14 min (method A). MS (ESI) (M+H)+ 703.24. The solvents were removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl-1-(3-(4-(allyloxy)phenyl)-3-(ethoxyimino)-propanoylimino)-2-(4-(2-bromoacetamido)-3,5-dichlorophenyl)ethylcarbamate (100 mg) in dichloromethane (0.30 mL) at room temperature was added pent-4-en-1-amine hydrochloride (51 mg) and diisopropylethylamine (97 μL), and the resulting solution was stirred at room temperature for 2 h. The solvents were removed in vacuo to give the title compound as a white solid, which was used in Step B without purification. retention time: 2.14 min (method A). MS (ESI) (M+H)+ 703.24. The solvents were removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Boc-piperidinone (1 g, 5 mmol) and tetrabutylammonium cyanate (2.86 g, 10 mmol) in MeOH (12 mL) was added cyclohexyl isocyanide (0.62 mL, 5 mmol) and pent-4-en-1-amine hydrochloride (732 mg, 6 mmol, prepared from the LAH reduction of 4-cyano-butene) in MeOH (8 mL) dropwise. The reaction mixture was stirred at rt for 1.5 h, diluted with EtOAC, washes with aq NaHCO3, brine, dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (silica gel, EtOAc) to provide the desired product LRMS (M+1)=419. diluted with EtOAC dried over sodium sulfate concentrated in vacuo purified by flash chromatography (silica gel, EtOAc)