ethyl (1R,3R,6S)-7-oxabicyclo[4.1.0]heptane-3-carboxylate

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (13.6 g) was dissolved in N,N-dimethyl-formamide (100 ml), ammonium chloride (6.45 g) and sodium azide (7.8 g) were successively added at room temperature, and the mixture was then stirred at 75° C. for 12 hours. The solvent was concentrated to about 1/3, and the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes. The resultant organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound (15.8 g) as a colorless oil. The solvent was concentrated to about 1/3 the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes The resultant organic layer was washed with water and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (13.6 g) was dissolved in N,N-dimethyl-formamide (100 ml), ammonium chloride (6.45 g) and sodium azide (7.8 g) were successively added at room temperature, and the mixture was then stirred at 75° C. for 12 hours. The solvent was concentrated to about 1/3, and the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes. The resultant organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound (15.8 g) as a colorless oil. The solvent was concentrated to about 1/3 the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes The resultant organic layer was washed with water and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

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

Procedure: (1R*,4R*,5R*)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-one (J. Org. Chem., 1996, Vol. 61, p. 8687) (14.3 g) was dissolved in ethanol (130 ml), a 2N aqueous solution (34.5 ml) of sodium hydroxide was added under ice cooling, and the mixture was then stirred at room temperature for 7 hours. After the solvent was distilled off under reduced pressure, and water was added to the residue to conduct extraction with dichloromethane, the extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17) to obtain the title compound (6.54 g) as a colorless oil. After the solvent was distilled off under reduced pressure, and water was added to the residue extraction with dichloromethane the extract was dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17)

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (13.6 g) was dissolved in N,N-dimethyl-formamide (100 ml), ammonium chloride (6.45 g) and sodium azide (7.8 g) were successively added at room temperature, and the mixture was then stirred at 75° C. for 12 hours. The solvent was concentrated to about 1/3, and the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes. The resultant organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound (15.8 g) as a colorless oil. The solvent was concentrated to about 1/3 the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes The resultant organic layer was washed with water and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

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

Procedure: (1R*,4R*,5R*)-4-Iodo-6-oxabicyclo [3.2.1]octan-7-one (J. Org. Chem., 1996, Vol. 61, p. 8687) (14.3 g) was dissolved in ethanol (130 ml), a 2N aqueous solution (34.5 ml) of sodium hydroxide was added under ice cooling, and the mixture was then stirred at room temperature for 7 hours. After the solvent was distilled off under reduced pressure, and water was added to the residue to conduct extraction with dichloromethane, the extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17) to obtain the title compound (6.54 g) as a colorless oil. After the solvent was distilled off under reduced pressure, and water was added to the residue extraction with dichloromethane the extract was dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17)

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

Procedure: (1R*,4R*,5R*)-4-Iodo-6-oxabicyclo [3.2.1]octan-7-one (J. Org. Chem., 1996, Vol. 61, p. 8687) (14.3 g) was dissolved in ethanol (130 ml), a 2N aqueous solution (34.5 ml) of sodium hydroxide was added under ice cooling, and the mixture was then stirred at room temperature for 7 hours. After the solvent was distilled off under reduced pressure, and water was added to the residue to conduct extraction with dichloromethane, the extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17) to obtain the title compound (6.54 g) as a colorless oil. After the solvent was distilled off under reduced pressure, and water was added to the residue extraction with dichloromethane the extract was dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17)

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

Procedure: (1R*,4R*,5R*)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-one (J. Org. Chem., vol. 61, p. 8687 (1996)) (14.3 g) was dissolved in ethanol (130 mL), and 2N aqueous sodium hydroxide (34.5 mL) was added to the solution under ice cooling, followed by stirring at room temperature for 7 hours. The solvent was distilled away under reduced pressure, and water was added to the residue. The mixture was extracted with methylene chloride, and the extract was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=83:17), to thereby give the title compound (6.54 g). The solvent was distilled away under reduced pressure, and water was added to the residue The mixture was extracted with methylene chloride the extract was dried over sodium sulfate anhydrate The solvent was distilled away under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=83:17)

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (13.6 g) was dissolved in N,N-dimethyl-formamide (100 ml), ammonium chloride (6.45 g) and sodium azide (7.8 g) were successively added at room temperature, and the mixture was then stirred at 75° C. for 12 hours. The solvent was concentrated to about 1/3, and the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes. The resultant organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound (15.8 g) as a colorless oil. The solvent was concentrated to about 1/3 the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes The resultant organic layer was washed with water and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

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

Procedure: (1R*,4R*,5R*)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-one (J. Org. Chem., 1996, Vol. 61, p. 8687) (14.3 g) was dissolved in ethanol (130 ml), a 2N aqueous solution (34.5 ml) of sodium hydroxide was added under ice cooling, and the mixture was then stirred at room temperature for 7 hours. After the solvent was distilled off under reduced pressure, and water was added to the residue to conduct extraction with dichloromethane, the extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17) to obtain the title compound (6.54 g) as a colorless oil. After the solvent was distilled off under reduced pressure, and water was added to the residue extraction with dichloromethane the extract was dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17)

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (13.6 g) was dissolved in N,N-dimethyl-formamide (100 ml), ammonium chloride (6.45 g) and sodium azide (7.8 g) were successively added at room temperature, and the mixture was then stirred at 75° C. for 12 hours. The solvent was concentrated to about 1/3, and the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes. The resultant organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound (15.8 g) as a colorless oil. The solvent was concentrated to about 1/3 the residue was diluted with water and ethyl acetate to conduct stirring for 3 minutes The resultant organic layer was washed with water and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

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

Procedure: (1R*,4R*,5R*)-4-Iodo-6-oxabicyclo [3.2.1]octan-7-one (J. Org. Chem., 1996, Vol. 61, p. 8687) (14.3 g) was dissolved in ethanol (130 ml), a 2N aqueous solution (34.5 ml) of sodium hydroxide was added under ice cooling, and the mixture was then stirred at room temperature for 7 hours. After the solvent was distilled off under reduced pressure, and water was added to the residue to conduct extraction with dichloromethane, the extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17) to obtain the title compound (6.54 g) as a colorless oil. After the solvent was distilled off under reduced pressure, and water was added to the residue extraction with dichloromethane the extract was dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=83:17)