[(2S)-2-(phenylmethoxycarbonylamino)propyl] methanesulfonate

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

Procedure: (S)-2-(Benzyloxycarbonylamino)propyl methanesulfonate (48 mmol) and cyclopropyl amine (480 mmol) were mixed together and stirred at room temperature for 48 h. The remaining cyclopropyl amine was removed by rotary evaporator and the residual mixture was added to 500 ml of ethyl acetate and washed with 5% Na2CO3 aqueous solution and brine. After drying (K2CO3) and removal of the solvent, the residual semi-solid was recrystallized from CH2Cl2 and petroleum ether to afford the target compound in 60% yield. The remaining cyclopropyl amine was removed by rotary evaporator the residual mixture was added to 500 ml of ethyl acetate washed with 5% Na2CO3 aqueous solution and brine After drying (K2CO3) and removal of the solvent the residual semi-solid was recrystallized from CH2Cl2 and petroleum ether to afford the target compound in 60% yield

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

Procedure: A solution of (S)-benzyl(1-hydroxypropan-2-yl)carbamate (400 g, 1.91 mol) and triethylamine (270 g, 2.67 mol) in methylene chloride (2.4 L) was cooled to 0° C. To this mixture was added methanesulfonyl chloride (263 g, 2.30 mol) at an internal temperature of 5° C. or below. Subsequently, the resulting reaction mixture was stirred at room temperature for 16 hours. After confirming the disappearance of the starting materials by TLC, to the reaction mixture was added purified water. The resulting organic layer was partitioned, washed with saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the target product as a yellow solid (519 g, yield 94.5%). Subsequently, the resulting reaction mixture to the reaction mixture was added purified water The resulting organic layer was partitioned washed with saturated brine dried over magnesium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: (S)-2-(Benzyloxycarbonylamino)propyl methanesulfonate (48 mmol) and cyclopropyl amine (480 mmol) were mixed together and stirred at room temperature for 48 h. The remaining cyclopropyl amine was removed by rotary evaporator and the residual mixture was added to 500 ml of ethyl acetate and washed with 5% Na2CO3 aqueous solution and brine. After drying (K2CO3) and removal of the solvent, the residual semi-solid was recrystallized from CH2Cl2 and petroleum ether to afford the target compound in 60% yield. The remaining cyclopropyl amine was removed by rotary evaporator the residual mixture was added to 500 ml of ethyl acetate washed with 5% Na2CO3 aqueous solution and brine After drying (K2CO3) and removal of the solvent the residual semi-solid was recrystallized from CH2Cl2 and petroleum ether to afford the target compound in 60% yield