(1S,2S)-cyclopentane-1,2-diol

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

Procedure: To a solution of (1S,2S)-cyclopentane-1,2-diol [manufactured by Fluka Co., cf. J. Org. Chem., 53, 1823 (1988)] (1.00 g) and 2,4-dichloroquinazoline (1.85 g) in dimethylformamide (9 ml) is added gradually 60% sodium hydride (in oil) (409 mg) with stirring under ice-cooling, and the mixture is stirred at room temperature for 1 hour and 20 minutes. The reaction mixture is diluted with ethyl acetate and washed with water 5 times. The resulting ethyl acetate solution is dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure, and the residue is briefly purified with medium pressure column chromatography (eluent, chloroform) to give an oily substance. The oily substance thus obtained is dissolved in dioxane (8 ml), and the mixture is slowly added dropwise to a solution of piperazine (2.21 g) in dioxane (10 ml) with stirring at 70° C., and the mixture is stirred at the same temperature for 40 minutes. The reaction mixture is diluted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. The resulting solution is evaporated to dryness under reduced pressure, and the residue is purified by medium pressure liquid column chromatography (eluent, chloroform:methanol=10:1, 5:1, v/v) to give 4-[(1S,2S)-(2-hydroxycyclopentan-1-yl)oxy]-2-(1-piperazinyl)-quinazoline (1.03 g) as crystals. cooling the mixture is stirred at room temperature for 1 hour and 20 minutes washed with water 5 times The resulting ethyl acetate solution is dried over anhydrous magnesium sulfate evaporated to dryness under reduced pressure the residue is briefly purified with medium pressure column chromatography (eluent, chloroform) to give an oily substance The oily substance thus obtained with stirring at 70° C. the mixture is stirred at the same temperature for 40 minutes washed with water dried over anhydrous magnesium sulfate The resulting solution is evaporated to dryness under reduced pressure the residue is purified by medium pressure liquid column chromatography (eluent, chloroform