[(R)-4-(二甲基氨基)-1-羟基-4-氧代丁烷-2-基]氨基甲酸苄酯

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 3-(S)-((carbobenzyloxy)amino)-γ-butyrolactone (prepared according to the procedure described in McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952, 7.72 g, 32.8 mmol) in THF (100 mL) was saturated with gaseous dimethylamine, stirred at room temperature for 16 hours, and concentrated. The residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes to give the desired product (9.16 g, 99%). MS (CI) m/e 281 (M+H)+. concentrated The residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 3-(S)-((carbobenzyloxy)amino)-γ-butyrolactone (prepared according to the procedure described in McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952, 7.72 g) in THF (100 mL) was saturated with gaseous dimethylamine, stirred at room temperature for 16 hours, and concentrated. The residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes to give the desired product. concentrated The residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of (R)-benzyl-5-oxotetrahydrofuran-3-ylcarbamate (INTERMEDIATE 3, 18.4 g, 7.8 mmol) in THF (100 ml) was purged, at room temperature, with gaseous dimethylamine for 5 minutes. After stirring at room temp for 14 hours, the reaction mixture was concentrated to dryness, and purified by column chromatography (silica gel, eluting first with 50% ethyl acetate/hexanes followed by 100% acetone) to give the title product (20 g, yield: 91.5%). the reaction mixture was concentrated to dryness purified by column chromatography (silica gel, eluting first with 50% ethyl acetate/hexanes followed by 100% acetone)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 3-(S)-((carbobenzyloxy)amino)-γ-butyrolactone (prepared according to the procedure described in McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952, 7.72 g) in THF (100 mL) was saturated with gaseous dimethylamine, stirred at room temperature for 16 hours, and concentrated. The residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes to give the desired product. concentrated The residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of (R)-benzyl-5-oxotetrahydrofuran-3-ylcarbamate (INTERMEDIATE 3, 18.4 g, 7.8 mmol) in THF (100 ml) was purged, at room temperature, with gaseous dimethylamine for 5 minutes. After stirring at room temp for 14 hours, the reaction mixture was concentrated to dryness, and purified by column chromatography (silica gel, eluting first with 50% ethyl acetate/hexanes followed by 100% acetone) to give the title product (20 g, yield: 91.5%). the reaction mixture was concentrated to dryness purified by column chromatography (silica gel, eluting first with 50% ethyl acetate/hexanes followed by 100% acetone)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 3-(S)-((carbobenzyloxy)amino)-γ-butyrolactone (prepared according to the procedure described in McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952, 7.72 g, 32.8 mmol) in THF (100 mL) was saturated with gaseous dimethylamine, stirred at room temperature for 16 hours, and concentrated. The residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes to give the desired product (9.16 g, 99%). MS (CI) m/e 281 (M+H)+. concentrated The residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes