2-ethoxyethyl methanesulfonate

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

Procedure: from 1.3 g of p-(2-ethoxyethoxy)-phenethylamine (prepared by the reaction of N-carbobenzoxytyramine in DMSO in the presence of potassium hydroxide with ethoxyethyl methanesulfonate and catalytic hydrogenation of the benzyl [p-(2-ethoxyethoxy)]phenethylcarbamate obtained in methanol in the presence of pd/C) and 726 mg of 3-[(RS)-2-oxiranyl]pyridine there were obtained

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

Procedure: from 1.3 g of p-(2-ethoxyethoxy)-phenethylamine (prepared by the reaction of N-carbobenzoxytyramine in DMSO in the presence of potassium hydroxide with ethoxyethyl methanesulfonate and catalytic hydrogenation of the benzyl [p-(2-ethoxyethoxy)]phenethylcarbamate obtained in methanol in the presence of pd/C) and 726 mg of 3-[(RS)-2-oxiranyl]pyridine there were obtained

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

Procedure: To 30g of 2-ethoxyethanol in 300ml of tetrahydrofuran 27.4ml of pyridine were added and 26.4ml of mesyl chloride added dropwise at room temperature over 15 minutes. The mixture was refluxed overnight, the solid that formed filtered off and the solvent evaporated off from the residue. The residue was distilled under 20m Hg to give 2-ethoxyethyl methanesulphonate. The mixture was refluxed overnight the solid that formed filtered off the solvent evaporated off from the residue The residue was distilled under 20m Hg

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

Procedure: 3.06 g of a 55% sodium hydride dispersion in oil were washed with hexane and covered with 85 ml of dimethylformamide. 17.0 g (71.6 mmol) of t-butyl [4-hydroxyphenethyl]carbamate [see F. Rocchiccioli et al., Tetrahedron, 34, 2917 (1978)] were then added while cooling with ice and the reaction mixture was stirred at room temperature for 15 minutes. After cooling to 0° a solution of 12.04 g (71.6 mmol) of 2-ethoxyethyl methanesulfonate in 85 ml of dimethylformamide was added dropwise within 10 minutes and the reaction mixture was subsequently stirred at room temperature for 24 hours. Thereafter, the reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride extracts were dried over magnesium sulfate and evaporated under reduced pressure. The residue obtained was chromatographed on 240 g of silica gel with a mixture of hexane and ethyl acetate as the eluting agent and subsequently recrystallized from ether/hexane, whereby there were obtained 19.1 g of t-butyl [ 4-(2-ethoxyethoxy)phenethyl]carbamate, melting point 56°-57°. 3.06 g of a 55% sodium hydride dispersion in oil were washed with hexane while cooling with ice was added dropwise within 10 minutes the reaction mixture was subsequently stirred at room temperature for 24 hours extracted with methylene chloride The methylene chloride extracts were dried over magnesium sulfate evaporated under reduced pressure The residue obtained was chromatographed on 240 g of silica gel with a mixture of hexane and ethyl acetate as the eluting agent subsequently recrystallized from ether/hexane

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

Procedure: from 1.3 g of p-(2-ethoxyethoxy)-phenethylamine (prepared by the reaction of N-carbobenzoxytyramine in DMSO in the presence of potassium hydroxide with ethoxyethyl methanesulfonate and catalytic hydrogenation of the benzyl [p-(2-ethoxyethoxy)]phenethylcarbamate obtained in methanol in the presence of pd/C) and 726 mg of 3-[(RS)-2-oxiranyl]pyridine there were obtained