methyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate

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

Procedure: A 1 N aqueous hydrochloric acid solution (50 mL)/acetone (200 ml) mixture of (1,4-dioxa-spiro[4.5]dec-8-yl)-acetic acid methyl ester (4.99 g) obtained in Example (1b) was stirred at room temperature for 15 hours. The organic solvent was removed using an evaporator. The remaining aqueous solution was subjected to two extractions with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated to obtain the title compound (4.30 g, quantitative yield) as a colorless oil. The organic solvent was removed an evaporator The remaining aqueous solution was subjected to two extractions with ethyl acetate The organic layer was washed with saturated brine dried over sodium sulfate concentrated

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

Procedure: A 1 N aqueous hydrochloric acid solution (50 mL)/acetone (200 ml) mixture of (1,4-dioxa-spiro[4.5]dec-8-yl)-acetic acid methyl ester (4.99 g) obtained in Example (1b) was stirred at room temperature for 15 hours. The organic solvent was removed using an evaporator. The remaining aqueous solution was subjected to two extractions with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated to obtain the title compound (4.30 g, quantitative yield) as a colorless oil. The organic solvent was removed an evaporator The remaining aqueous solution was subjected to two extractions with ethyl acetate The organic layer was washed with saturated brine dried over sodium sulfate concentrated

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

Procedure: An ethanol (50 mL) suspension of (1,4-dioxa-spiro[4.5]dec-8-ylidene)-acetic acid methyl ester (6.57 g) obtained in Example (1a) and palladium carbon (10% by weight) was hydrogen-reduced at room temperature for 24 hours. The reaction mixture was filtered and concentrated. The residue was purified by chromatography (hexane/ethyl acetate=5:1) to obtain the title compound (4.99 g, 75%) as a colorless oil. The reaction mixture was filtered concentrated The residue was purified by chromatography (hexane/ethyl acetate=5:1)

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

Procedure: A suspension of 0.76 g of lithium aluminum hydride in 10 mL of tetrahydrofuran was cooled to 0° C. under a nitrogen atmosphere. To the suspension was added dropwise a solution of 2.18 g of methyl 1,4-dioxaspiro[4.5]decane-8-acetate in 10 mL of tetrahydrofuran, followed by stirring at room temperature for 3 hours. After the reaction mixture was cooled to 0° C., 1 mL of water was added thereto. The mixture was filtered through celite and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.73 g of 1,4-dioxaspiro[4.5]decane-8-ethanol represented by the following formula: After the reaction mixture was cooled to 0° C. The mixture was filtered through celite concentrated under reduced pressure

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

Procedure: A 1 N aqueous hydrochloric acid solution (50 mL)/acetone (200 ml) mixture of (1,4-dioxa-spiro[4.5]dec-8-yl)-acetic acid methyl ester (4.99 g) obtained in Example (1b) was stirred at room temperature for 15 hours. The organic solvent was removed using an evaporator. The remaining aqueous solution was subjected to two extractions with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated to obtain the title compound (4.30 g, quantitative yield) as a colorless oil. The organic solvent was removed an evaporator The remaining aqueous solution was subjected to two extractions with ethyl acetate The organic layer was washed with saturated brine dried over sodium sulfate concentrated

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

Procedure: An ethanol (50 mL) suspension of (1,4-dioxa-spiro[4.5]dec-8-ylidene)-acetic acid methyl ester (6.57 g) obtained in Example (1a) and palladium carbon (10% by weight) was hydrogen-reduced at room temperature for 24 hours. The reaction mixture was filtered and concentrated. The residue was purified by chromatography (hexane/ethyl acetate=5:1) to obtain the title compound (4.99 g, 75%) as a colorless oil. The reaction mixture was filtered concentrated The residue was purified by chromatography (hexane/ethyl acetate=5:1)