benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (3-Hydroxy-1-(S)-methyl-propyl)-carbamic acid benzyl ester (8.02 g, 35.9 mmol) was taken up in DMF (75 mL). tert-Butyl-dimethylsilyl chloride (8.12 g, 53.9 mmol) was added to the solution followed by imidazole (4.15 g, 61.0 mmol). The reaction was stirred at rt and monitored by TLC. The reaction was determined to be complete at 1 h by TLC. The reaction was taken up in EtOAc (200 mL) and partitioned between 5% LiCl(aq) (200 mL). The aqueous was back extracted with EtOAc. The organics were combined and washed with 3×200 mL 5% LiCl(aq), and dried over Na2SO4. Solids were filtered and solvent removed under reduced pressure. [3-(tert-Butyl-silanoxy)-1-(S)-methyl-propyl]-carbamic acid benzyl ester (12.73 g, 100%) was isolated by silica gel chromatography as a white solid. partitioned between 5% LiCl(aq) (200 mL) The aqueous was back extracted with EtOAc washed with 3×200 mL 5% LiCl(aq) dried over Na2SO4 Solids were filtered solvent removed under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (1-(S)-Methyl-allyl)-carbamic acid benzyl ester (1.96 g, 9.56 mmol) was taken up in THF (200 mL). 9-BBN 0.5M in THF (38 mL, 19.0 mmol) was added slowly to the reaction mixture. The solution was allowed to stir at rt for 16 h. Quenched with H2O (65 mL), followed by 1.0M NaOH(aq) (20 mL). The solution was cooled to 0° C. in an ice bath and H2O2 30% in H2O (7.0 mL) was slowly added. The reaction was partitioned between Et2O and H2O. The layers were separated and the aqueous washed with Et2O. The combine organics were dried over Na2SO4. Solids were filtered and the solvent removed under reduced pressure. (3-hydroxy-1-(S)-methyl-propyl)-carbamic acid benzyl ester (1.85 g, 87%) was isolated by silica gel chromatography as a white solid. Quenched with H2O (65 mL) The solution was cooled to 0° C. in an ice bath H2O2 30% in H2O (7.0 mL) was slowly added The reaction was partitioned between Et2O and H2O The layers were separated the aqueous washed with Et2O The combine organics were dried over Na2SO4 Solids were filtered the solvent removed under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (3-Hydroxy-1-(S)-methyl-propyl)-carbamic acid benzyl ester (8.02 g, 35.9 mmol) was taken up in DMF (75 mL). tert-Butyl-dimethylsilyl chloride (8.12 g, 53.9 mmol) was added to the solution followed by imidazole (4.15 g, 61.0 mmol). The reaction was stirred at rt and monitored by TLC. The reaction was determined to be complete at 1 h by TLC. The reaction was taken up in EtOAc (200 mL) and partitioned between 5% LiCl(aq) (200 mL). The aqueous was back extracted with EtOAc. The organics were combined and washed with 3×200 mL 5% LiCl(aq), and dried over Na2SO4. Solids were filtered and solvent removed under reduced pressure. [3-(tert-Butyl-silanoxy)-1-(S)-methyl-propyl]-carbamic acid benzyl ester (12.73 g, 100%) was isolated by silica gel chromatography as a white solid. partitioned between 5% LiCl(aq) (200 mL) The aqueous was back extracted with EtOAc washed with 3×200 mL 5% LiCl(aq) dried over Na2SO4 Solids were filtered solvent removed under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (1-(S)-Methyl-allyl)-carbamic acid benzyl ester (1.96 g, 9.56 mmol) was taken up in THF (200 mL). 9-BBN 0.5M in THF (38 mL, 19.0 mmol) was added slowly to the reaction mixture. The solution was allowed to stir at rt for 16 h. Quenched with H2O (65 mL), followed by 1.0M NaOH(aq) (20 mL). The solution was cooled to 0° C. in an ice bath and H2O2 30% in H2O (7.0 mL) was slowly added. The reaction was partitioned between Et2O and H2O. The layers were separated and the aqueous washed with Et2O. The combine organics were dried over Na2SO4. Solids were filtered and the solvent removed under reduced pressure. (3-hydroxy-1-(S)-methyl-propyl)-carbamic acid benzyl ester (1.85 g, 87%) was isolated by silica gel chromatography as a white solid. Quenched with H2O (65 mL) The solution was cooled to 0° C. in an ice bath H2O2 30% in H2O (7.0 mL) was slowly added The reaction was partitioned between Et2O and H2O The layers were separated the aqueous washed with Et2O The combine organics were dried over Na2SO4 Solids were filtered the solvent removed under reduced pressure