1-(2-hydroxyethyl)cyclopentan-1-ol

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

Procedure: 1,4-dibromobutane (10 g, 46.3 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg) as initiator. The mixture was stirred at rt for 3 h. To the mixture was added dropwise oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL). The reaction was stirred at rt for 12 h, quenched with saturated NH4Cl, and the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The organic layers were combined and dried over MgSO4, filtered and concentrated. The residue was purified by distillation at 95-100° C.@0.6 Torr to provide the title compound (1.1 g, 18%). MS (DCI/NH3) m/z 148 (M+NH4)+. The reaction was stirred at rt for 12 h quenched with saturated NH4Cl the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL) dried over MgSO4 filtered concentrated The residue was purified by distillation at 95-100° C.

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

Procedure: A solution of 1,4-dibromobutane (10 g, 46 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg). The mixture was stirred at room temperature for 3 hours a solution of oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL) was added dropwise. The reaction mixture was stirred at room temperature for 12 hours then quenched with saturated aqueous NH4Cl and extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified by distillation (95-100° C. at 0.6 Torr) to provide 1.1 g (18%) of the title compound. MS (DCI/NH3) m/z 148 (M+NH4)+. was added dropwise then quenched with saturated aqueous NH4Cl extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL) The combined organic extracts were dried over MgSO4 filtered concentrated The residue was purified by distillation (95-100° C. at 0.6 Torr)

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

Procedure: A solution of 1,4-dibromobutane (10 g, 46 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg). The mixture was stirred at room temperature for 3 hours a solution of oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL) was added dropwise. The reaction mixture was stirred at room temperature for 12 hours then quenched with saturated aqueous NH4Cl and extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified by distillation (95-100° C. at 0.6 Torr) to provide 1.1 g (18%) of the title compound. MS (DCI/NH3) m/z 148 (M+NH4)+. was added dropwise then quenched with saturated aqueous NH4Cl extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL) The combined organic extracts were dried over MgSO4 filtered concentrated The residue was purified by distillation (95-100° C. at 0.6 Torr)

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

Procedure: 1,4-dibromobutane (10 g, 46.3 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg) as initiator. The mixture was stirred at room temperature for 3 hours. To the mixture was added dropwise oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL). The reaction was stirred at room temperature for 12 hours, quenched with saturated NH4Cl, and the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The organic layers were combined and dried over MgSO4, filtered and concentrated. The residue was purified by distillation at 95-100° C. (0.6 torr) to provide the title compound (1.1 g, 18%) MS (DCI/NH3) m/z 148 (M+NH4)+. The reaction was stirred at room temperature for 12 hours quenched with saturated NH4Cl the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL) dried over MgSO4 filtered concentrated The residue was purified by distillation at 95-100° C. (0.6 torr)

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

Procedure: 1,4-dibromobutane (10 g, 46.3 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg) as initiator. The mixture was stirred at room temperature for 3 hours. To the mixture was added dropwise oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL). The reaction was stirred at room temperature for 12 hours, quenched with saturated NH4Cl, and the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The organic layers were combined and dried over MgSO4, filtered and concentrated. The residue was purified by distillation at 95-100° C. (0.6 torr) to provide the title compound (1.1 g, 18%) MS (DCI/NH3) m/z 148 (M+NH4)+. The reaction was stirred at room temperature for 12 hours quenched with saturated NH4Cl the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL) dried over MgSO4 filtered concentrated The residue was purified by distillation at 95-100° C. (0.6 torr)

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

Procedure: 1,4-dibromobutane (10 g, 46.3 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg) as initiator. The mixture was stirred at rt for 3 h. To the mixture was added dropwise oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL). The reaction was stirred at rt for 12 h, quenched with saturated NH4Cl, and the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The organic layers were combined and dried over MgSO4, filtered and concentrated. The residue was purified by distillation at 95-100° C.@0.6 Torr to provide the title compound (1.1 g, 18%). MS (DCI/NH3) m/z 148 (M+NH4)+. The reaction was stirred at rt for 12 h quenched with saturated NH4Cl the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL) dried over MgSO4 filtered concentrated The residue was purified by distillation at 95-100° C.

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

Procedure: A solution of 1,4-dibromobutane (10 g, 46 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg). The mixture was stirred at room temperature for 3 hours a solution of oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL) was added dropwise. The reaction mixture was stirred at room temperature for 12 hours then quenched with saturated aqueous NH4Cl and extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified by distillation (95-100° C. at 0.6 Torr) to provide 1.1 g (18%) of the title compound. MS (DCI/NH3) m/z 148 (M+NH4)+. was added dropwise then quenched with saturated aqueous NH4Cl extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL) The combined organic extracts were dried over MgSO4 filtered concentrated The residue was purified by distillation (95-100° C. at 0.6 Torr)

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

Procedure: To a solution of 1-(2-hydroxyethyl)cyclopentanol (19 0 mg, 1.46 mmol) in dry dichloromethane (2 mL) was added methanesulfonyl chloride (200.3 mg, 1.75 mmol) dropwise at 0° C., followed by TEA (295 mg, 2.92 mmol). Then the mixture was stirred at room temperature 1 h. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product (50 mg, 31.1% yield), which was used without purification. The mixture was partitioned between ethyl acetate and water The organic phase was washed with brine dried over sodium sulfate filtered concentrated

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

Procedure: To a solution of tert-butyl 2-(1-hydroxycyclopentyl)acetate (0.5 g, 2.5 mmol) in THF (10 mL) was added lithium aluminium hydride (0.28 g, 7.5 mmol) portionwise at 0° C. The reaction was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether/ethyl acetate (1:1) to give 1-(2-hydroxyethyl)cyclopentanol (0.33 g, 100%) as a yellow oil. The mixture was partitioned between ethyl acetate and water The combined organic layer was dried over sodium sulfate filtered concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether/ethyl acetate (1:1)

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

Procedure: A solution of 1,4-dibromobutane (10 g, 46 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg). The mixture was stirred at room temperature for 3 hours a solution of oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL) was added dropwise. The reaction mixture was stirred at room temperature for 12 hours then quenched with saturated aqueous NH4Cl and extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified by distillation (95-100° C. at 0.6 Ton) to provide 1.1 g (18%) of the title compound. MS (DCI/NH3) m/z 148 (M+NH4)−. was added dropwise then quenched with saturated aqueous NH4Cl extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL) The combined organic extracts were dried over MgSO4 filtered concentrated The residue was purified by distillation (95-100° C. at 0.6 Ton)

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

Procedure: 1,4-dibromobutane (10 g, 46.3 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg) as initiator. The mixture was stirred at room temperature for 3 hours. To the mixture was added dropwise oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL). The reaction was stirred at room temperature for 12 hours, quenched with saturated NH4Cl, and the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The organic layers were combined and dried over MgSO4, filtered and concentrated. The residue was purified by distillation at 95-100° C. (0.6 torr) to provide the title compound (1.1 g, 18%) MS (DCI/NH3) m/z 148 (M+NH4)+. The reaction was stirred at room temperature for 12 hours quenched with saturated NH4Cl the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL) dried over MgSO4 filtered concentrated The residue was purified by distillation at 95-100° C. (0.6 torr)