[(1S,6R)-6-(hydroxymethyl)cyclohex-3-en-1-yl]methanol

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

Procedure: A solution of the anhydride of 3,4-dicarboxycyclohex-1-ene (25.8 g) in THF (150 ml) is added with cooling to a stirred suspension of LiAlH4 (9 g) in THF (200 ml) under N2 at a rate such as to maintain the temperature at 0° C. After stirring for 18 hours at room temperature the mixture is gently refluxed for one hour and cooled in ice. The excess lithium aluminium hydride is decomposed by the careful addition of 1:1 THF-H2O mixture (100 ml). After dilution with chloroform (150 ml) the resulting mixture is filtered and the solid is washed with chloroform (3×25 ml). Concentration of the filtrate under reduced pressure yields an oily residue which is dissolved in benzene, dried over (MgSO4) and reconcentrated in vacuo to give the title compound as an oil (22 g, ca. 90%), νmax (film) 3350 cm-1. is gently refluxed for one hour cooled in ice After dilution with chloroform (150 ml) the resulting mixture is filtered the solid is washed with chloroform (3×25 ml) Concentration of the filtrate under reduced pressure yields an oily residue which dried over (MgSO4)

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

Procedure: A solution of the anhydride of 3,4-dicarboxycyclohex-1-ene (25.8 g) in THF (150 ml) is added with cooling to a stirred suspension of LiAlH4 (9 g) in THF (200 ml) under N2 at a rate such as to maintain the temperature at 0° C. After stirring for 18 hours at room temperature the mixture is gently refluxed for one hour and cooled in ice. The excess lithium aluminium hydride is decomposed by the careful addition of 1:1 THF-H2O mixture (100 ml). After dilution with chloroform (150 ml) the resulting mixture is filtered and the solid is washed with chloroform (3×25 ml). Concentration of the filtrate under reduced pressure yields an oily residue which is dissolved in benzene, dried over (MgSO4) and reconcentrated in vacuo to give the title compound as an oil (22 g, ca. 90%), νmax (film) 3350 cm-1. is gently refluxed for one hour cooled in ice After dilution with chloroform (150 ml) the resulting mixture is filtered the solid is washed with chloroform (3×25 ml) Concentration of the filtrate under reduced pressure yields an oily residue which dried over (MgSO4)

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

Procedure: The diol (1) (16.2 g) in dimethylformamide (50 ml) is added dropwise to sodium hydride (3.1 g) in dimethylformamide (DMF) (50 ml). The mixture is stirred for 20 minutes and then benzyl chloride (16 g) is added and stirring is continued for a further 18 hours at 70° C. After removing the DMF in vacuo, water is added and the mixture is extracted with ether. The combined extracts are dried (MgSO4) and the solvent is evaporated to give a residue which is distilled under reduced pressure to give the title compound as an oil (16.5 g, ca. 60%), b.p. 140°-145° C./0.03 mm, νmax (film) 3440 and 1600 cm-1. stirring is continued for a further 18 hours at 70° C After removing the DMF in vacuo, water is added the mixture is extracted with ether The combined extracts are dried (MgSO4) the solvent is evaporated to give a residue which is distilled under reduced pressure

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

Procedure: The diol (1) (16.2 g) in dimethylformamide (50 ml) is added dropwise to sodium hydride (3.1 g) in dimethylformamide (DMF) (50 ml). The mixture is stirred for 20 minutes and then benzyl chloride (16 g) is added and stirring is continued for a further 18 hours at 70° C. After removing the DMF in vacuo, water is added and the mixture is extracted with ether. The combined extracts are dried (MgSO4) and the solvent is evaporated to give a residue which is distilled under reduced pressure to give the title compound as an oil (16.5 g, ca. 60%), b.p. 140°-145° C./0.03 mm, νmax (film) 3440 and 1600 cm-1. stirring is continued for a further 18 hours at 70° C After removing the DMF in vacuo, water is added the mixture is extracted with ether The combined extracts are dried (MgSO4) the solvent is evaporated to give a residue which is distilled under reduced pressure

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

Procedure: A solution of the anhydride of 3,4-dicarboxycyclohex-1-ene (25.8 g) in THF (150 ml) is added with cooling to a stirred suspension of LiAlH4 (9 g) in THF (200 ml) under N2 at a rate such as to maintain the temperature at 0° C. After stirring for 18 hours at room temperature the mixture is gently refluxed for one hour and cooled in ice. The excess lithium aluminium hydride is decomposed by the careful addition of 1:1 THF-H2O mixture (100 ml). After dilution with chloroform (150 ml) the resulting mixture is filtered and the solid is washed with chloroform (3×25 ml). Concentration of the filtrate under reduced pressure yields an oily residue which is dissolved in benzene, dried over (MgSO4) and reconcentrated in vacuo to give the title compound as an oil (22 g, ca. 90%), νmax (film) 3350 cm-1. is gently refluxed for one hour cooled in ice After dilution with chloroform (150 ml) the resulting mixture is filtered the solid is washed with chloroform (3×25 ml) Concentration of the filtrate under reduced pressure yields an oily residue which dried over (MgSO4)

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

Procedure: The diol (1) (16.2 g) in dimethylformamide (50 ml) is added dropwise to sodium hydride (3.1 g) in dimethylformamide (DMF) (50 ml). The mixture is stirred for 20 minutes and then benzyl chloride (16 g) is added and stirring is continued for a further 18 hours at 70° C. After removing the DMF in vacuo, water is added and the mixture is extracted with ether. The combined extracts are dried (MgSO4) and the solvent is evaporated to give a residue which is distilled under reduced pressure to give the title compound as an oil (16.5 g, ca. 60%), b.p. 140°-145° C./0.03 mm, νmax (film) 3440 and 1600 cm-1. stirring is continued for a further 18 hours at 70° C After removing the DMF in vacuo, water is added the mixture is extracted with ether The combined extracts are dried (MgSO4) the solvent is evaporated to give a residue which is distilled under reduced pressure

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

Procedure: (25.8 g) in THF (150 ml) is added with cooling to a stirred suspension of LiAlH4 (9 g) in THF (200 ml) under N2 at a rate such as to maintain the temperature at 0° C. After stirring for 18 hours at room temperature the mixture is gently refluxed for one hour and cooled in ice. The excess lithium aluminium hydride is decomposed by the careful addition of 1:1 THF-H2O mixture (100 ml). After dilution with chloroform (150 ml) the resulting mixture is filtered and the solid is washed with chloroform (3×25 ml). Concentration of the filtrate under reduced pressure yields an oily residue which is dissolved in benzene, dried over (MgSO4) and reconcentrated in vacuo to give the title compound as an oil (22 g, ca. 90%), νmax (film) 3350 cm-1. is gently refluxed for one hour cooled in ice After dilution with chloroform (150 ml) the resulting mixture is filtered the solid is washed with chloroform (3×25 ml) Concentration of the filtrate under reduced pressure yields an oily residue which dried over (MgSO4)

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

Procedure: A solution of 25 g of cis-4-cyclohexene-1,2-dicarboxylic acid anhydride in 140 ml of tetrahydrofuran is instilled in a suspension of 10 g of lithium aluminum hydride in 140 ml of tetrahydrofuran at room temperature and the mixture is then stirred for 3 hours at reflux temperature. It is cooled to 0° C. a mixture of tetrahydrofuran/water (1+1) is instilled slowly, stirred for 30 minutes, mixed with 150 ml of chloroform, filtered and the filtrate is concentrated by evaporation in a vacuum. The residue is distilled at 0.2 mm/Torr and 150° C. on a bulb tube. After recrystallization of the distillate from toluene/pentane, 21 g of cis-1,6-dihydroxymethyl-3-cyclohexene is obtained as colorless crystals, melting point 33°-35° C. at reflux temperature stirred for 30 minutes filtered the filtrate is concentrated by evaporation in a vacuum The residue is distilled at 0.2 mm/Torr and 150° C. on a bulb tube After recrystallization of the distillate from toluene/pentane

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

Procedure: The diol (1) (16.2 g) in dimethylformamide (50 ml) is added dropwise to sodium hydride (3.1 g) in dimethylformamide (DMF) (50 ml). The mixture is stirred for 20 minutes and then benzyl chloride (16 g) is added and stirring is continued for a further 18 hours at 70° C. After removing the DMF in vacuo, water is added and the mixture is extracted with ether. The combined extracts are dried (MgSO4) and the solvent is evaporated to give a residue which is distilled under reduced pressure to give the title compound as an oil (16.5 g, ca. 60%), b.p. 140°-145° C./0.03 mm, λmax (film) 3440 and 1600 cm-1. stirring is continued for a further 18 hours at 70° C After removing the DMF in vacuo, water is added the mixture is extracted with ether The combined extracts are dried (MgSO4) the solvent is evaporated to give a residue which is distilled under reduced pressure

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

Procedure: A solution of the anhydride of 3,4-dicarboxycyclohex-1-ene (25.8 g) in THF (150 ml) is added with cooling to a stirred suspension of LiA1H4 (9 g) in THF (200 ml) under N2 at a rate such as to maintain the temperature at 0° C. After stirring for 18 hours at room temperature the mixture is gently refluxed for one hour and cooled in ice. The excess lithium aluminium hydride is decomposed by the careful addition of 1:1 THF-H2O mixture (100 ml). After dilution with chloroform (150 ml) the resulting mixture is filtered and the solid is washed with chloroform (3×25 ml). Concentration of the filtrate under reduced pressure yields an oily residue which is dissolved in benzene, dried over (MgSO4) and reconcentrated in vacuo to give the title compound as an oil (22 g, ca. 90%), λmax (film) 3350 cm-1. is gently refluxed for one hour cooled in ice After dilution with chloroform (150 ml) the resulting mixture is filtered the solid is washed with chloroform (3×25 ml) Concentration of the filtrate under reduced pressure yields an oily residue which dried over (MgSO4)

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

Procedure: The diol (1) (16.2 g) in dimethylformamide (50 ml) is added dropwise to sodium hydride (3.1 g) in dimethylformamide (DMF) (50 ml). The mixture is stirred for 20 minutes and then benzyl chloride (16 g) is added and stirring is continued for a further 18 hours at 70° C. After removing the DMF in vacuo, water is added and the mixture is extracted with ether. The combined extracts are dried (MgSO4) and the solvent is evaporated to give a residue which is distilled under reduced pressure to give the title compound as an oil (16.5 g, ca. 60%), b.p. 140°-145° C./0.03 mm, νmax (film) 3440 and 1600 cm-1. stirring is continued for a further 18 hours at 70° C After removing the DMF in vacuo, water is added the mixture is extracted with ether The combined extracts are dried (MgSO4) the solvent is evaporated to give a residue which is distilled under reduced pressure

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

Procedure: A solution of the anhydride of 3,4-dicarboxycyclohex-1-ene (25.8 g) in THF (150 ml) is added with cooling to a stirred suspension of LiAlH4 (9 g) in THF (200 ml) under N2 at a rate such as to maintain the temperature at 0° C. After stirring for 18 hours at room temperature the mixture is gently refluxed for one hour and cooled in ice. The excess lithium aluminium hydride is decomposed by the careful addition of 1:1 THF-H2O mixture (100 ml). After dilution with chloroform (150 ml) the resulting mixture is filtered and the solid is washed with chloroform (3×25 ml). Concentration of the filtrate under reduced pressure yields an oily residue which is dissolved in benzene, dried over (MgSO4) and reconcentrated in vacuo to give the title compound as an oil (22 g, ca. 90%), νmax (film) 3350 cm-1. is gently refluxed for one hour cooled in ice After dilution with chloroform (150 ml) the resulting mixture is filtered the solid is washed with chloroform (3×25 ml) Concentration of the filtrate under reduced pressure yields an oily residue which dried over (MgSO4)