tert-butyl N-[2-(hydroxymethyl)butyl]carbamate

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

Procedure: Oxalyl chloride (141 μL) was dissolved in methylene chloride (1 mL). To the solution, a solution of dimethyl sulfoxide (176 μL) in methylene chloride (1 mL) was added dropwise at −78° C., and the mixture was stirred for 15 minutes. A solution of the compound (168 mg) obtained in Step 5 in methylene chloride (2 mL) was added dropwise thereto at −78° C., and the mixture was stirred for 2 hours. Triethylamine (695 μL) was added thereto, and the mixture was heated to 0° C. and then stirred overnight. To the reaction solution, methylene chloride was added, and the organic layer was washed with water and saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=9/1-7/3) to obtain the title compound (113 mg). at −78° C., and the mixture was stirred for 2 hours stirred overnight the organic layer was washed with water and saturated sodium chloride solution dried over anhydrous sodium sulfate filtered The solvent was distilled off under reduced pressure The obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=9/1-7/3)

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

Procedure: Lithium aluminum hydride (153 mg) was suspended in tetrahydrofuran (20 mL). To the suspension, a solution of the compound obtained in Step 4 in tetrahydrofuran (2 mL) was added dropwise under ice cooling, and the mixture was then stirred overnight. To the reaction solution, sodium sulfate decahydrate was added under ice cooling. Subsequently, ethyl acetate was added thereto, and the mixture was stirred. After celite filtration, the solvent in the filtrate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=9/1-3/7) to obtain the title compound (168 mg). the mixture was stirred After celite filtration the solvent in the filtrate was distilled off under reduced pressure The obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=9/1-3/7)