3-(甲硫基)-4-氧代-4,5,6,7-四氢苯并〔C)噻吩-1-羧酸乙酯

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5.42 g (18.1 mmol) of ethyl 4-adamantan-1-yl-phenylcarbamate were treated with 1.43 g (18.1 mmol) of pyridine and 18.0 g (0.136 mol) of (RS)-4-methoxymethyl-1,3-dioxolan-2-one and stirred at 160° bath temperature for 20 hours. After cooling the reaction mixture was chromatographed on 500 g of silica gel 60 with ether. 1.4 g of (RS)-3-(4-adamantan-1-yl)phenyl]-5-methoxymethyl-oxazolidin-2-one were obtained as a white crystallizate after recrystallization from methylene chloride/ether. M.p.: 145°-147°. After cooling the reaction mixture was chromatographed on 500 g of silica gel 60 with ether

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 932 mg (2.6 mmol) of (R)-3-[trans-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-cyclohexyloxy]-propionitrile were dissolved in 60 ml of methanol saturated with dry ammonia gas and hydrogenated in the presence of 0.9 g of Raney-nickel (Type B 113W Degussa). After 3 hours the catalyst was filtered off under suction and the filtrate was evaporated. The residue was dissolved in methylene chloride, washed with water, dried over sodium sulfate, filtered and evaporated. The base was dissolved in alcohol and made acid with ethereal hydrochloric acid. After recrystallization from alcohol-ether there were obtained 825.2 mg of (R)-3-[trans-4-(3-amino-propoxy)-cyclohexyl]-phenyl]-5-methoxymethyl-oxazolidin-2-one.HCl. M.p.: 178°-180°. [α]D =-29.78° (c=1% in CHCl3). After 3 hours the catalyst was filtered off under suction the filtrate was evaporated The residue was dissolved in methylene chloride washed with water dried over sodium sulfate filtered evaporated The base was dissolved in alcohol After recrystallization from alcohol-ether

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: By reaction and treatment in the same manner as in Preparation Example 25 and using 1-amino-3-methoxypropan-2-ol (1 g), 5-methoxymethyloxazolidin-2-one (620 mg) was obtained. To a mixture of 5-methoxymethyloxazolidin-2-one (620 mg), ethyl 4-iodobenzoate (1.6 mL), potassium carbonate (2.6 g) and copper (I) iodide (552 mg) were added toluene (20 mL) and N,N′-dimethylethylenediamine (625 μL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated to give the title compound (830 mg). the mixture was refluxed for 8 hr After cooling the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine the solvent was evaporated

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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