[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH:12]1[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=O)C.O>O1CCCC1>[CH3:21][S:18]([N:15]1[CH2:16][CH2:17][CH:12]([CH2:10][OH:9])[CH2:13][CH2:14]1)(=[O:20])=[O:19]A solution of 1.0 M lithium aluminum hydride (200 ml, 0.2 mole) in tetrahydrofuran was added dropwise to a solution of 1-methanesulfonylpiperidine-4-carboxylic acid ethyl ester (68 grams, 0.29 mole) in tetrahydrofuran (500 ml) at about +5° C. The reaction mixture was stirred at 5-10° C. for 15 minutes. Water (10 ml) was added dropwise and the mixture was filtered. The filtrate was concentrated under reduced pressure and triturated with 50% ethyl ether-hexane (100 ml). The resulting white solid was collected and dried to give 1-methanesulfonylpiperidine-4-methanol (46 grams, 82%), m.p. 96-97° C.
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