tert-butyl 4-hydroxy-4-(oxiran-2-ylmethyl)piperidine-1-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1.42 g of 4-(2,3-epoxypropan-1-yl)-1-(tert-butoxycarbonyl)piperidin-4-ol in dimethyl sulfoxide (20 ml) were added in a nitrogen atmosphere 5 ml of water and 2.32 g of lithium hydroxide and the resulting mixture was heated to 140° C. for 30 minutes. After adding ethyl acetate, the reaction mixture was washed with water thrice. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate) to thereby give 0.336 g of the title compound as colorless crystals. the reaction mixture was washed with water thrice The organic layer was dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4.115 g of 4-allyl-1-(tert-butoxycarbonyl)piperidin-4-ol in dichloromethane (100 ml) were added 7.07 g of 3-chloroperbenzoic acid and 2.87 g of sodium hydrogencarbonate and the resulting mixture was heated under reflux for 24 hours. To the reaction mixture were added ethyl acetate and an aqueous solution of sodium metabisulfite and the resulting mixture was stirred for 1 hour. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate) to thereby give 1.43 g of the title compound as a colorless solid. the resulting mixture was heated under reflux for 24 hours The organic layer was dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4.115 g of 4-allyl-1-(tert-butoxycarbonyl)piperidin-4-ol in dichloromethane (100 ml) were added 7.07 g of 3-chloroperbenzoic acid and 2.87 g of sodium hydrogencarbonate and the resulting mixture was heated under reflux for 24 hours. To the reaction mixture were added ethyl acetate and an aqueous solution of sodium metabisulfite and the resulting mixture was stirred for 1 hour. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate) to thereby give 1.43 g of the title compound as a colorless solid. the resulting mixture was heated under reflux for 24 hours The organic layer was dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-allyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (3.1 g, 12.8 mmol, prepared according to J. Comb. Chem. 2002, 4, 125) in DCM and 0.3 M phosphate buffer (pH 8, 150 mL) was treated with mCPBA (3.5 g, 1.1 eq, 70%) and the mixture vigorously stirred at rt overnight. Further 3.5 g of mCPBA were added. After a total of 24 h, the phases were separated, the org. phase dried over MgSO4 and concentrated. CC (hex/EA 2:1 to 1:1 to EA) gave the desired intermediate as colourless oil (0.88 g, 26%). After a total of 24 h, the phases were separated phase dried over MgSO4 concentrated

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1.42 g of 4-(2,3-epoxypropan-1-yl)-1-(tert-butoxycarbonyl)piperidin-4-ol in dimethyl sulfoxide (20 ml) were added in a nitrogen atmosphere 5 ml of water and 2.32 g of lithium hydroxide and the resulting mixture was heated to 140° C. for 30 minutes. After adding ethyl acetate, the reaction mixture was washed with water thrice. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate) to thereby give 0.336 g of the title compound as colorless crystals. the reaction mixture was washed with water thrice The organic layer was dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4.115 g of 4-allyl-1-(tert-butoxycarbonyl)piperidin-4-ol in dichloromethane (100 ml) were added 7.07 g of 3-chloroperbenzoic acid and 2.87 g of sodium hydrogencarbonate and the resulting mixture was heated under reflux for 24 hours. To the reaction mixture were added ethyl acetate and an aqueous solution of sodium metabisulfite and the resulting mixture was stirred for 1 hour. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate) to thereby give 1.43 g of the title compound as a colorless solid. the resulting mixture was heated under reflux for 24 hours The organic layer was dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate)