4-(methoxymethyl)-1,3-dioxolan-2-one

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

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

Procedure: A mixture of 14 g (0.132 mol) of 3-methoxypropane-1,2-diol (S)and 31.16 g (0.264 mol) of diethyl carbonate in the presence of 0.108 g of 50% sodium hydride is heated until distillation of the alcohol formed. After completion of the reaction, the aimed product is distilled. formed After completion of the reaction the aimed product is distilled

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

Procedure: A mixture of 14 g (0.132 mol) of compound 370487 (Method 2--Step 2), 31.16 g (0.264 mol) of diethyl carbonate in the presence of 0.108 g of 50% sodium hydride is heated until distillation of the alcohol formed. After completion of the reaction, the aimed product is distilled. formed After completion of the reaction the aimed product is distilled

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

Procedure: A mixture of 14 g (0.132 mol) of compound 370487 (Method 2--Step 2), 31.16 g (0.264 mol) of diethyl carbonate in the presence of 0.108 g of 50% sodium hydride is heated until distillation of the alcohol formed. After completion of the reaction, the aimed product is distilled. formed After completion of the reaction the aimed product is distilled

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Urethane (10.0 g, 113 mmol) was dissolved in N,N-dimethylformamide (40 ml), and thereto were added sodium methoxide (409 mg, 7.57 mmol) and 4-methoxymethyl-1,3-dioxolan-2-one (10.0 g, 75.7 mmol), in order. The mixture was stirred for 80 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by silica gel chromatography to give the subject 5-methoxymethyloxazolidin-2-one (4.3 g, yield 43.3%). After filtering off the insoluble materials condensed in vacuo the residue was purified by silica gel chromatography

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Urethane (10.0 g, 113 mmol) was dissolved in N,N-dimethylformamide (40 ml), and thereto were added potassium carbonate (20.8 g, 151 mmol) and 4-methoxymethyl-1,3-dioxolan-2-one (10.0 g, 75.7 mmol), in order. The mixture was stirred for 100 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by silica gel chromatography give the subject 5-methoxymethyloxazolidin-2-one (2.3g, yield 23.1%). After filtering off the insoluble materials condensed in vacuo the residue was purified by silica gel chromatography

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylurethane (15.0 g, 90.9 mmol) was dissolved in N,N-dimethylformamide (40 mL), and thereto were added cesium fluoride (1.15 g, 7.57 mmol) and 4-methoxymethyl-1,3-dioxolan-2-one (10.0 g, 75.7 mol), in order. The mixture was stirred for 50 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by silica gel chromatography to give the subject 3-phenyl-5-methoxymethyloxazolidin-2-one (12.8 g, yield 81.6%). After filtering off the insoluble materials condensed in vacuo the residue was purified by silica gel chromatography

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylurethane (15.0 g, 90.9 mmol) was dissolved in N,N-dimethylformamide (40 mL), and thereto were added cesium fluoride (1.15 g, 7.57 mmol) and 4-methoxymethyl-1,3-dioxolan-2-one (10.0 g, 75.7 mol), in order. The mixture was stirred for 50 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by silica gel chromatography to give the subject 3-phenyl-5-methoxymethyloxazolidin-2-one (12.8 g, yield 81.6%). After filtering off the insoluble materials condensed in vacuo the residue was purified by silica gel chromatography

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Urethane (82.4 g, 0.925 mol) was dissolved in dimethyl sulfoxide (400 mL), and thereto were added potassium fluoride (48.8 g, 0.841 mol) and 4-methoxymethyl-1,3-dioxolan-2-one (111 g, 0.841 mol), in order. The mixture was stirred for 77 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by distillation to give the subject 5-methoxymethyloxazolidin-2-one (76.0 g, yield 68.9%). After filtering off the insoluble materials condensed in vacuo the residue was purified by distillation

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Urethane (82.4 g, 0.925 mol) was dissolved in dimethyl sulfoxide (400 mL), and thereto were added potassium fluoride (48.8 g, 0.841 mol) and 4-methoxymethyl-1,3-dioxolan-2-one (111 g, 0.841 mol), in order. The mixture was stirred for 77 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by distillation to give the subject 5-methoxymethyloxazolidin-2-one (76.0 g, yield 68.9%). After filtering off the insoluble materials condensed in vacuo the residue was purified by distillation

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

Procedure: A mixture of 16.8 g of ethyl pyridin-3-yl-carbamate, 20 g of 4-methoxymethyl-1,3-dioxolan-2-one and 2.8 g of potassium carbonate was heated to 160° for 3 h. The mixture was cooled and treated with ethyl acetate and water. The phases were separated, the aqueous phase was extracted with ethyl acetate and the organic phase was washed with saturated sodium chloride solution. The organic phases were combined, dried with magnesium sulfate and concentrated. Chromatography of the residue (21 g) on silica gel with ethyl acetate/methanol mixtures (1:0-20:1) yielded 17.6 g of (RS)-5-methoxymethyl-3-pyridin-3-yl-oxazolidin-2-one which was recrystallized from diethyl ether. M.p.: 65°-66°. was heated to 160° for 3 h The mixture was cooled The phases were separated the aqueous phase was extracted with ethyl acetate the organic phase was washed with saturated sodium chloride solution dried with magnesium sulfate concentrated

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

Procedure: 1.12 g (3.5 mmol) of ethyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylate were treated with 4.0 g (30.28 mmol) of (RS)-4-(methoxymethyl)-1,3-dioxolan-2-one in the presence of 276.8 mg (3.5 mmol) of pyridine and stirred intensively for 18 hours at an oil bath temperature of 160°. After cooling the reaction mixture was chromatographed on 125 g of silica gel 60 with ether. After recrystallization from methylene chloride/isopropyl ether there were obtained 976 mg of ethyl (RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine-1-carboxylate. M.p.: 86°-88°. After cooling the reaction mixture was chromatographed on 125 g of silica gel 60 with ether After recrystallization from methylene chloride/isopropyl ether there