[BH4-].[Li+].C([O:5][C:6]([C:8]1([C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][N:19]=2)[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH2:9]1)=O)C.[Cl-].[NH4+]>O1CCCC1>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:8]2([CH2:6][OH:5])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[N:19][CH:20]=1Lithium borohydride (1.71 g) was added at room temperature to a solution of 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4.5]decane-8-carboxylic acid ethyl ester (7.26 g) described in Reference Example 81(2) in tetrahydrofuran (100 ml) and stirred at the same temperature for 39 hours. Then, lithium borohydride (855 mg) was added and stirred at the same temperature for 24 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give [8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4.5]dec-8-yl]methanol (5.17 g) as a colorless transparent oil.
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