Cyclohexanecarboxylic acid, 1-methyl-4-oxo-, ethyl ester

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 8-Methyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (Compound 282G) was dissolved in THF (20 mL) and 3N aq. HCl (30 mL). The resulting mixture was stirred at rt overnight. The mixture was diluted with EtOAc (50 mL), washed with brine (20 mL), and dried over anhydrous sodium sulfate. 1H NMR (CDCl3): 1.28 (t, J=7.1 Hz, 3H), 1.29 (s, 3H), 1.63-1.70 (m, 2H), 2.30-2.74 (m, 6H), 3.94 (s, 4H), 4.19 (q, J=7.1 Hz, 2H). washed with brine (20 mL) dried over anhydrous sodium sulfate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 8-Methyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (Compound 282G) was dissolved in THF (20 mL) and 3N aq. HCl (30 mL). The resulting mixture was stirred at rt overnight. The mixture was diluted with EtOAc (50 mL), washed with brine (20 mL), and dried over anhydrous sodium sulfate. 1H NMR (CDCl3): 1.28 (t, J=7.1 Hz, 3H), 1.29 (s, 3H), 1.63-1.70 (m, 2H), 2.30-2.74 (m, 6H), 3.94 (s, 4H), 4.19 (q, J=7.1 Hz, 2H). washed with brine (20 mL) dried over anhydrous sodium sulfate

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

Procedure: Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate (Int-18b, 2.09 g, 9.17 mmol) was dissolved in acetonitrile (100 mL) and water (50 mL). Ammonium cerium nitrate (503 mg, 0.92 mmol) in water (50 mL) was added and the resulting mixture was heated up to 70° C. and stirred for 1 h. After being cooled down to room temperature, water (100 mL) was added and the mixture was extracted with ether (100 mL×3). The combined organics were washed with water, brine and dried. After concentration, the residue was purified on a column (silica gel, 0-30% ethyl acetate in hexane) which gave ethyl 1-methyl-4-oxocyclohexanecarboxylate (Int-18c) (1.72 g) as an oil. After being cooled down to room temperature the mixture was extracted with ether (100 mL×3) The combined organics were washed with water, brine dried After concentration the residue was purified on a column (silica gel, 0-30% ethyl acetate in hexane) which

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

Procedure: In a 50 mL round-bottom flask was mixed with ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate (Int-6a, 1.99 g, 8.72 mmol), EtOH (10 mL), H2O (5 mL), and 4N HCl in 1,4-dioxane (5 mL). The resulting solution was stirred at room temperature for 64 hours. At this time, the solvent was removed in vacuo and the residue was taken up in DCM. The suspension was washed with saturated NaHCO3(aq) and the organic layer was dried over Na2SO4. The resulting product was taken on without further purification. Yield=1.00 g. At this time, the solvent was removed in vacuo The suspension was washed with saturated NaHCO3(aq) the organic layer was dried over Na2SO4 The resulting product was taken on without further purification

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

Procedure: 8-Methyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (Compound 282G) was dissolved in THF (20 mL) and 3N aq. HCl (30 mL). The resulting mixture was stirred at rt overnight. The mixture was diluted with EtOAc (50 mL), washed with brine (20 mL), and dried over anhydrous sodium sulfate. 1H NMR (CDCl3): 1.28 (t, J=7.1 Hz, 3H), 1.29 (s, 3H), 1.63-1.70 (m, 2H), 2.30-2.74 (m, 6H), 3.94 (s, 4H), 4.19 (q, J=7.1 Hz, 2H). washed with brine (20 mL) dried over anhydrous sodium sulfate

Conditions: temp:0.00; pressure:0.00; stir: