(1S,2R)-cyclopentane-1,2-diol

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

Procedure: Prepared analogously to III.1 from cis-1,2-cyclopentandiol (1.0 g) and 1.28 ml 2,4-difluoronitrobenzene.

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

Procedure: A solution of the compound (0.10 g, 0.25 mmol) of Example 21, (1R,2S)-1,2-cyclopentanediol (0.26 g, 2.5 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.012 g, 0.012 mmol) in N,N-dimethylacetamide (1.5 mL) was stirred with the microwave synthesizer (Biotage Initiator™) at 130° C. for 2 h. Cooled to ambient temperature, the precipitate was removed by filtration. The filtrate was purified by preparative HPLC to afford the titled compound as solid (0.025 g, y. 20%). the precipitate was removed by filtration The filtrate was purified by preparative HPLC

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 19.4 g (0.19 mol) of cis-1,2-cyclopentanediol were added dropwise to a suspension of 4.8 g (0.2 mol) of sodium hydride (6.0 g of 80% pure sodium hydride in toluene) in 200 ml of dioxan at 5° C. under a nitrogen atmosphere, whilst stirring. After the evolution of hydrogen had ended, the mixture was warmed to 70° C. for 45 minutes and then brought to room temperature and 359 g (0.19 mol) of 2-fluorobenzyl bromide in absolute dioxan were added. After stirring the mixture for 30 minutes, it was heated to the boil for a further 4 hours and cooled and about 10 ml of methanol were added. The mixture was concentrated to dryness on a rotary evaporator, the residue was taken up in water and the mixture was extracted with methylene chloride. The organic phase was dried over sodium sulphate and filtered and the solvent was stripped off from the filtrate on a rotary evaporator. The oily residue was distilled under an oil pump vacuum. 18.4 g (46% of theory) of cis-1-(2-fluorobenzyloxy)-cyclopentan-2-ol of boiling point 95°-100° C./0.1 mm Hg were obtained. brought to room temperature After stirring the mixture for 30 minutes it was heated to the boil for a further 4 hours cooled The mixture was concentrated to dryness on a rotary evaporator the mixture was extracted with methylene chloride The organic phase was dried over sodium sulphate filtered the solvent was stripped off from the filtrate on a rotary evaporator The oily residue was distilled under an oil pump vacuum

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

Procedure: Prepared analogously to III.1 from cis-1,2-cyclopentandiol (1.0 g) and 1.28 ml 2,4-difluoronitrobenzene.

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

Procedure: A solution of the compound (0.10 g, 0.25 mmol) of Example 21, (1R,2S)-1,2-cyclopentanediol (0.26 g, 2.5 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.012 g, 0.012 mmol) in N,N-dimethylacetamide (1.5 mL) was stirred with the microwave synthesizer (Biotage Initiator™) at 130° C. for 2 h. Cooled to ambient temperature, the precipitate was removed by filtration. The filtrate was purified by preparative HPLC to afford the titled compound as solid (0.025 g, y. 20%). the precipitate was removed by filtration The filtrate was purified by preparative HPLC

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

Procedure: Particularly preferred compounds of this invention are 5-norbornene-2,2-dimethanol; norbornane-2,2-dimethanol; 2-norbornanemethanol; 1,2-cis-cyclopentanediol; 2,3-cis-exo-norbornanediol, 2-(propyl-1,2-diol)-norbornane and 3,3-dimethyl-1,2-butanediol. Other preferred compounds are 1,2-trans-cyclopentanediol; 2,3-dimethyl-2,3-butanediol; 2-methyl-1,3-propanediol; 2,3-butanediol; and propylene glycol.

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

Procedure: Particularly preferred compounds of this invention are 5-norbornene-2,2-dimethanol; norbornane-2,2-dimethanol; 2-norbornanemethanol; 1,2-cis-cyclopentanediol; 2,3-cis-exo-norbornanediol, 2-(propyl-1,2-diol)-norbornane and 3,3-dimethyl-1,2-butanediol. Other preferred compounds are 1,2-trans-cyclopentanediol; 2,3-dimethyl-2,3-butanediol; 2-methyl-1,3-propanediol; 2,3-butanediol; and propylene glycol.

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

Procedure: Particularly preferred compounds of this invention are 5-norbornene-2,2-dimethanol; norbornane-2,2-dimethanol; 2-norbornanemethanol; 1,2-cis-cyclopentanediol; 2,3-cis-exo-norbornanediol, 2-(propyl-1,2-diol)-norbornane and 3,3-dimethyl-1,2-butanediol. Other preferred compounds are 1,2-trans-cyclopentanediol; 2,3-dimethyl-2,3-butanediol; 2-methyl-1,3-propanediol; 2,3-butanediol; and propylene glycol.

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 19.4 g (0.19 mol) of cis-1,2-cyclopentanediol were added dropwise to a suspension of 4.8 g (0.2 mol) of sodium hydride (6.0 g of 80% pure sodium hydride in toluene) in 200 ml of dioxan at 5° C. under a nitrogen atmosphere, whilst stirring. After the evolution of hydrogen had ended, the mixture was warmed to 70° C. for 45 minutes and then brought to room temperature and 359 g (0.19 mol) of 2-fluorobenzyl bromide in absolute dioxan were added. After stirring the mixture for 30 minutes, it was heated to the boil for a further 4 hours and cooled and about 10 ml of methanol were added. The mixture was concentrated to dryness on a rotary evaporator, the residue was taken up in water and the mixture was extracted with methylene chloride. The organic phase was dried over sodium sulphate and filtered and the solvent was stripped off from the filtrate on a rotary evaporator. The oily residue was distilled under an oil pump vacuum. 18.4 g (46% of theory) of cis-1-(2-fluorobenzyloxy)-cyclopentan-2-ol of boiling point 95°-100° C./0.1 mm Hg were obtained. brought to room temperature After stirring the mixture for 30 minutes it was heated to the boil for a further 4 hours cooled The mixture was concentrated to dryness on a rotary evaporator the mixture was extracted with methylene chloride The organic phase was dried over sodium sulphate filtered the solvent was stripped off from the filtrate on a rotary evaporator The oily residue was distilled under an oil pump vacuum

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

Procedure: Prepared analogously to III.1 from cis-1,2-cyclopentandiol (1.0 g) and 1.28 ml 2,4-difluoronitrobenzene.

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

Procedure: A solution of the compound (0.10 g, 0.25 mmol) of Example 21, (1R,2S)-1,2-cyclopentanediol (0.26 g, 2.5 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.012 g, 0.012 mmol) in N,N-dimethylacetamide (1.5 mL) was stirred with the microwave synthesizer (Biotage Initiator™) at 130° C. for 2 h. Cooled to ambient temperature, the precipitate was removed by filtration. The filtrate was purified by preparative HPLC to afford the titled compound as solid (0.025 g, y. 20%). the precipitate was removed by filtration The filtrate was purified by preparative HPLC