tert-butyl N-[(2R)-1-cyclohexyl-3-hydroxypropan-2-yl]carbamate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of Example 1A (25.8 g,100 mmol), sulfur trioxide pyridine complex (79.6 g, 500 mmol), and triethylamine (69.7 mL, 500 mmol) in DMSO (70 mL) at room temperature was stirred for 30 minutes, cooled to 0° C., treated with water and saturated aqueous KHSO4, and extracted with ethyl acetate. The extract was washed with saturated aqueous KHSO4 and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. extracted with ethyl acetate The extract was washed with saturated aqueous KHSO4 and brine dried (MgSO4) filtered concentrated

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

Procedure: A solution of (2R)-2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoic acid (30.4 g, 112 mmol) in toluene (300 mL) at 0° C. was treated with sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al®) (115 mmol) over 45 minutes. The mixture was stirred for 30 minutes, warmed to room temperature, stirred for 1 hour, treated with aqueous Rochelle salt, and extracted with diethyl ether. The extract was washed with brine and aqueous NaHCO3, dried (MgSO4), filtered, and concentrated to provide the desired product. stirred for 1 hour extracted with diethyl ether The extract was washed with brine and aqueous NaHCO3 dried (MgSO4) filtered concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of Example 3A (25.8 g, 100 mmol), sulfur trioxide pyridine complex (79.6 g, 500 mmol), and triethylamine (69.7 mL, 500 mmol) in DMSO (70 mL) at room temperature was stirred for 30 minutes, cooled to 0° C., treated with water and saturated aqueous KHSO4, and extracted with ethyl acetate. The extract was washed sequentially with saturated aqueous KHSO4 and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. extracted with ethyl acetate The extract was washed sequentially with saturated aqueous KHSO4 and brine dried (MgSO4) filtered concentrated

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

Procedure: A solution of (2R)-2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoic acid (30.4 g, 112 mmol) in toluene (300 mL) at 0° C. was treated with sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al®) (115 mmol) over 45 minutes. The mixture was stirred for 30 minutes, warmed to room temperature, stirred for 1 hour, treated with aqueous Rochelle salt, and extracted with diethyl ether. The extract was washed sequentially with brine and aqueous NaHCO3, dried (MgSO4), filtered, and concentrated to provide the desired product. stirred for 1 hour extracted with diethyl ether The extract was washed sequentially with brine and aqueous NaHCO3 dried (MgSO4) filtered concentrated